Dextromethorphan Hydrobromide → Dextromethorphan tannate

HRID 433953Notes

Reaction equation

HRID 433953 reaction equation
[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.Br.[CH:22]1[C:27]([OH:28])=[C:26]([OH:29])[C:25]([OH:30])=[CH:24][C:23]=1[C:31]([O:33][C:34]1[CH:35]=[C:36]([C:42]([O:44][CH2:45][C@H:46]2[O:51][C@@H:50]([O:52][C:53]([C:55]3[CH:56]=[C:57]([OH:74])[C:58]([OH:73])=[C:59]([O:61][C:62]([C:64]4[CH:65]=[C:66]([OH:72])[C:67]([OH:71])=[C:68]([OH:70])[CH:69]=4)=[O:63])[CH:60]=3)=[O:54])[C@H:49]([O:75][C:76]([C:78]3[CH:79]=[C:80]([OH:97])[C:81]([OH:96])=[C:82]([O:84][C:85]([C:87]4[CH:88]=[C:89]([OH:95])[C:90]([OH:94])=[C:91]([OH:93])[CH:92]=4)=[O:86])[CH:83]=3)=[O:77])[C@@H:48]([O:98][C:99]([C:101]3[CH:102]=[C:103]([OH:120])[C:104]([OH:119])=[C:105]([O:107][C:108]([C:110]4[CH:111]=[C:112]([OH:118])[C:113]([OH:117])=[C:114]([OH:116])[CH:115]=4)=[O:109])[CH:106]=3)=[O:100])[C@@H:47]2[O:121][C:122]([C:124]2[CH:125]=[C:126]([OH:143])[C:127]([OH:142])=[C:128]([O:130][C:131]([C:133]3[CH:134]=[C:135]([OH:141])[C:136]([OH:140])=[C:137]([OH:139])[CH:138]=3)=[O:132])[CH:129]=2)=[O:123])=[O:43])[CH:37]=[C:38]([OH:41])[C:39]=1[OH:40])=[O:32]>>[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:22]1[C:27]([OH:28])=[C:26]([OH:29])[C:25]([OH:30])=[CH:24][C:23]=1[C:31]([O:33][C:34]1[C:39]([OH:40])=[C:38]([OH:41])[CH:37]=[C:36]([C:42]([O:44][CH2:45][C@H:46]2[O:51][C@@H:50]([O:52][C:53]([C:55]3[CH:60]=[C:59]([O:61][C:62]([C:64]4[CH:69]=[C:68]([OH:70])[C:67]([OH:71])=[C:66]([OH:72])[CH:65]=4)=[O:63])[C:58]([OH:73])=[C:57]([OH:74])[CH:56]=3)=[O:54])[C@H:49]([O:75][C:76]([C:78]3[CH:83]=[C:82]([O:84][C:85]([C:87]4[CH:92]=[C:91]([OH:93])[C:90]([OH:94])=[C:89]([OH:95])[CH:88]=4)=[O:86])[C:81]([OH:96])=[C:80]([OH:97])[CH:79]=3)=[O:77])[C@@H:48]([O:98][C:99]([C:101]3[CH:106]=[C:105]([O:107][C:108]([C:110]4[CH:111]=[C:112]([OH:118])[C:113]([OH:117])=[C:114]([OH:116])[CH:115]=4)=[O:109])[C:104]([OH:119])=[C:103]([OH:120])[CH:102]=3)=[O:100])[C@@H:47]2[O:121][C:122]([C:124]2[CH:129]=[C:128]([O:130][C:131]([C:133]3[CH:138]=[C:137]([OH:139])[C:136]([OH:140])=[C:135]([OH:141])[CH:134]=3)=[O:132])[C:127]([OH:142])=[C:126]([OH:143])[CH:125]=2)=[O:123])=[O:43])[CH:35]=1)=[O:32]

Participants

3

Reactant 2

HCID 5464025Dextromethorphan Hydrobromide2×HCID 16129778Tannic Acid

Product 1

HCID 16214284Dextromethorphan tannate

Procedure

The filtrate was evaporated to dryness and the resultant solid (about 12 g) was then dried. The dried solid had a melting point of about 121° C. which compared quite closely to the melting point of 123° C. for pure dextromethorphan-HBr which indicated that the tannic acid had not reacted with the dextromethorphan-HBr. A sample of the dried solid was then subject to FTIR analysis and the spectrum which was obtained was then compared to the FTIR spectrum of pure dextromethorphan HBR. The two spectra were nearly identical. Therefore, it is clear that the dextromethorphan-HBr did not react with the tannic acid to form dextromethorphan tannate and that the dextromethorphan-HBr was present as a mixture with the tannic acid.

Workup

  1. customThe filtrate was evaporated to dryness
  2. dry with materialthe resultant solid (about 12 g) was then dried
  3. customhad not reacted with the dextromethorphan-HBr
  4. customthe spectrum which was obtained

Sources & evidence

ORD record
ord-15f580d076c1430ca7b521563457b5f5
Source dataset
uspto-grants-2003_12
Patent number
US06670370B1

Reaction notes

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