Chlorpheniramine Maleate → (+-)-Chlorpheniramine

HRID 1194278Notes

Reaction equation

HRID 1194278 reaction equation
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:19]=1)[C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1)[CH3:3].C(/C(O)=O)=C/C(O)=O>O.[OH-].[NH4+]>[CH3:1][N:2]([CH2:4][CH2:5][CH:6]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][N:19]=1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)[CH3:3]

Participants

4

Reactant 1

HCID 5281068Chlorpheniramine Maleate

Product 1

HCID 2725(+-)-Chlorpheniramine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

Chlorpheniramine maleate, 15 g, is dissolved in 150 ml of water, to which about 20 ml of ammonium hydroxide is added. The resulting precipitate is extracted with diethyl ether (2×50 ml), washed with water, and dried with anhydrous sodium sulfate. The diethyl ether is evaporated under a stream of nitrogen to give chlorpheniramine free base. The chlorpheniramine free base is dissolved in a mixture of linoleic acid, propylene glycol, and triacetin. The previous mixture is uniformly dispersed in a mixture of medical grade dimethylsiloxane and dibutyl tin dilaurate. The resulting mixture is casted as a membrane on a smooth Teflon surface in a mold and allowed to cure at room temperature for about eighteen hours. The resulting material is applied as a film on adhesive tape.

Workup

  1. additionis added
  2. extractionThe resulting precipitate is extracted with diethyl ether (2×50 ml)
  3. washwashed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe diethyl ether is evaporated under a stream of nitrogen

Sources & evidence

ORD record
ord-ddf0d91a40c24f719530e1c772192bbf
Source dataset
uspto-grants-1989_03
Patent number
US04814173

Reaction notes

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