HRID433954

反应详情

EQUATION

反应方程式

REACTANTS

反应物

结构：COc1ccc2c(c1)[C@]13CCCC[C@@H]1[C@H](C2)N(C)CC3

HCID5360696

Dextromethorphan

C18H25NO

3 次

结构：Br.COc1ccc2c(c1)[C@]13CCCC[C@@H]1[C@H](C2)N(C)CC3

HCID5464025

Dextromethorphan hydrobromide

C18H26BrNO

结构：O=C(OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H]1OC(=O)c1cc(O)c(O)c(OC(=O)c2cc(O)c(O)c(O)c2)c1)c1cc(O)c(O)c(OC(=O)c2cc(O)c(O)c(O)c2)c1

HCID16129778

Chinese gallotannin

C76H52O46

2 次

PRODUCTS

生成物

结构：COc1ccc2c(c1)[C@]13CCCC[C@@H]1[C@H](C2)N(C)CC3.O=C(OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H](OC(=O)c2cc(O)c(O)c(OC(=O)c3cc(O)c(O)c(O)c3)c2)[C@@H]1OC(=O)c1cc(O)c(O)c(OC(=O)c2cc(O)c(O)c(O)c2)c1)c1cc(O)c(O)c(OC(=O)c2cc(O)c(O)c(O)c2)c1

HCID16214284

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

CONDITIONS

反应条件

温度: 90 °C

PROCEDURE

实验过程

14 g of dextromethorphan free base was mixed with 12 g of water and 36 g of tannate acid. The mixture was heated with stirring, to 90° C. and maintained at such temperature for several minutes. After cooling to room temperature, the reaction product was dried and powdered. A sample of the powdered product was mixed with methylene chloride, but no dissolution occurred, indicating that the reaction product did not consist of dextromethorphan free base. A sample of the reaction product was dried to a moisture (K.F.) level of about 4% and it was determined that such material had a softening point of about 100° C. (in comparison to the sharp melting point of 123° C. for dextromethorphan-HBr, the melting point of 109.5-112.5° C. for dextromethorphan free base and the decomposition point of 210-215° C. for tannic acid). The reaction product was also subjected to FTIR analysis and the spectrum obtained thereby was quite different from that of either dextromethorphan free base or tannic acid (or dextromethorphan-HBr). Therefore, it is clear that when dextromethorphan free base is reacted with tannic acid in accordance with the process of the invention, a unique type of dextromethorphan tannate product is obtained.

WORKUP

后处理

temperatureThe mixture was heated
temperaturemaintained at such temperature for several minutes
temperatureAfter cooling to room temperature
customthe reaction product was dried
additionA sample of the powdered product was mixed with methylene chloride
dissolutionno dissolution
customA sample of the reaction product was dried to a moisture (K.F.) level of about 4% and it
customa softening point of about 100° C.
customthe spectrum obtained

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-c1e861eed741445394aa923ca308529f
来源数据集: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06670370B1
来源说明: uspto-grants-2003_12

反应 SMILES

[CH3:1][N:2]1[C@H:11]2[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[C@:5]3([C@@H:10]2[CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:4][CH2:3]1.[CH:21]1[C:26]([OH:27])=[C:25]([OH:28])[C:24]([OH:29])=[CH:23][C:22]=1[C:30]([O:32][C:33]1[CH:34]=[C:35]([C:41]([O:43][CH2:44][C@H:45]2[O:50][C@@H:49]([O:51][C:52]([C:54]3[CH:55]=[C:56]([OH:73])[C:57]([OH:72])=[C:58]([O:60][C:61]([C:63]4[CH:64]=[C:65]([OH:71])[C:66]([OH:70])=[C:67]([OH:69])[CH:68]=4)=[O:62])[CH:59]=3)=[O:53])[C@H:48]([O:74][C:75]([C:77]3[CH:78]=[C:79]([OH:96])[C:80]([OH:95])=[C:81]([O:83][C:84]([C:86]4[CH:87]=[C:88]([OH:94])[C:89]([OH:93])=[C:90]([OH:92])[CH:91]=4)=[O:85])[CH:82]=3)=[O:76])[C@@H:47]([O:97][C:98]([C:100]3[CH:101]=[C:102]([OH:119])[C:103]([OH:118])=[C:104]([O:106][C:107]([C:109]4[CH:110]=[C:111]([OH:117])[C:112]([OH:116])=[C:113]([OH:115])[CH:114]=4)=[O:108])[CH:105]=3)=[O:99])[C@@H:46]2[O:120][C:121]([C:123]2[CH:124]=[C:125]([OH:142])[C:126]([OH:141])=[C:127]([O:129][C:130]([C:132]3[CH:133]=[C:134]([OH:140])[C:135]([OH:139])=[C:136]([OH:138])[CH:137]=3)=[O:131])[CH:128]=2)=[O:122])=[O:42])[CH:36]=[C:37]([OH:40])[C:38]=1[OH:39])=[O:31].CN1[C@H]2CC3C=CC(OC)=CC=3[C@]3([C@@H]2CCCC3)CC1.Br>O>[CH3:1][N:2]1[C@H:11]2[CH2:12][C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=3[C@:5]3([C@@H:10]2[CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:4][CH2:3]1.[CH:21]1[C:26]([OH:27])=[C:25]([OH:28])[C:24]([OH:29])=[CH:23][C:22]=1[C:30]([O:32][C:33]1[C:38]([OH:39])=[C:37]([OH:40])[CH:36]=[C:35]([C:41]([O:43][CH2:44][C@H:45]2[O:50][C@@H:49]([O:51][C:52]([C:54]3[CH:59]=[C:58]([O:60][C:61]([C:63]4[CH:68]=[C:67]([OH:69])[C:66]([OH:70])=[C:65]([OH:71])[CH:64]=4)=[O:62])[C:57]([OH:72])=[C:56]([OH:73])[CH:55]=3)=[O:53])[C@H:48]([O:74][C:75]([C:77]3[CH:82]=[C:81]([O:83][C:84]([C:86]4[CH:91]=[C:90]([OH:92])[C:89]([OH:93])=[C:88]([OH:94])[CH:87]=4)=[O:85])[C:80]([OH:95])=[C:79]([OH:96])[CH:78]=3)=[O:76])[C@@H:47]([O:97][C:98]([C:100]3[CH:105]=[C:104]([O:106][C:107]([C:109]4[CH:110]=[C:111]([OH:117])[C:112]([OH:116])=[C:113]([OH:115])[CH:114]=4)=[O:108])[C:103]([OH:118])=[C:102]([OH:119])[CH:101]=3)=[O:99])[C@@H:46]2[O:120][C:121]([C:123]2[CH:128]=[C:127]([O:129][C:130]([C:132]3[CH:137]=[C:136]([OH:138])[C:135]([OH:139])=[C:134]([OH:140])[CH:133]=3)=[O:131])[C:126]([OH:141])=[C:125]([OH:142])[CH:124]=2)=[O:122])=[O:42])[CH:34]=1)=[O:31]