Hydrochloric Acid → 2-Methoxy-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamine hydrochloride
Reaction equation
[CH:1]([N:3](C)[CH:4]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[O:12][CH3:13])=O.[ClH:21]>CO>[ClH:21].[CH3:13][O:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH2:5][CH:4]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[NH:3][CH3:1]Participants
4
Procedure
A solution of 1.83 g of N-formyl-2-methoxy-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, 25 ml of methanol, and 25 ml of 3N hydrochloric acid solution was heated for 3 hr under reflux. Methanol was added to clear the solution. The solution was concentrated, the residue was diluted with water, and extracted with ether. The aqueous phase was basified with 2.5N sodium hydroxide solution and extracted with dichloromethane. The combined organic phase was dried over anhydrous sodium sulfate, filtered, and concentrated. An ether solution of the residue was treated with excess ethereal hydrogen chloride. Recrystallization from acetonitrile gave 0.83 g of product, mp 201°-203.5° C.
Workup
- temperatureunder reflux
- concentrationThe solution was concentrated
- additionthe residue was diluted with water
- extractionextracted with ether
- extractionextracted with dichloromethane
- dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- additionAn ether solution of the residue was treated with excess ethereal hydrogen chloride
- customRecrystallization from acetonitrile
Sources & evidence
- ORD record
- ord-31dead035bcb42b9af0321c355bd9169
- Source dataset
- uspto-grants-1994_03
- Patent number
- US05292760
Reaction notes
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