Dextromethorphan → Dextromethorphan tannate

HRID 433954

反応式

HRID 433954 の反応式
[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]

参加物

5

反応物 3

HCID 5360696Dextromethorphan3 回HCID 5464025Dextromethorphan HydrobromideHCID 16129778Tannic Acid2 回

生成物 1

HCID 16214284Dextromethorphan tannate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-c1e861eed741445394aa923ca308529f
出典データセット
uspto-grants-2003_12
特許番号
US06670370B1

関連ノート

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