Benzene → HCID 86733836, compound
Reaction equation
[C:1]1(C)[CH:6]=[CH:5][C:4]([C:7]([Cl:9])=[O:8])=[CH:3][CH:2]=1.NC[C:13]1([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH2:22]([N:24](CC)CC)C.Cl.[CH:30]1C=CC=CC=1>>[ClH:9].[CH3:30][CH:16]1[CH2:15][CH2:14][CH:13]([N:19]([CH3:20])[CH2:21][CH2:22][NH:24][C:7](=[O:8])[C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[CH2:18][CH2:17]1Participants
Procedure
A solution of p-toluoyl chloride (1 g.) 1-aminomethylcyclohexyl dimethylamine (1 g.) and triethylamine (0.65 g.) in benzene (60 ml.) was heated under reflux for 1.5 hrs. The excess benzene was evaporated under reduced pressure, the residue dissolved in water and extracted with chloroform. The extracts were dried (anhyd. sodium sulphate) and the chloroform evaporated under reduced pressure to give an oil which solidified on cooling. Excess ethereal hydrochloric acid was added to an ethereal solution of the solid and the excess ether removed under reduced pressure. The solid residue was crystallised from isopropanol/petroleum ether (80-100) to give 4-methylbenzamido methyl cyclohexyl dimethylamine hydrochloride m.p. 199°-201° (0.7 g.).
Workup
- temperatureunder reflux for 1.5 hrs
- customThe excess benzene was evaporated under reduced pressure
- dissolutionthe residue dissolved in water
- extractionextracted with chloroform
- dry with materialThe extracts were dried (anhyd. sodium sulphate)
- customthe chloroform evaporated under reduced pressure
- customto give an oil which
- temperatureon cooling
- customthe excess ether removed under reduced pressure
- customThe solid residue was crystallised from isopropanol/petroleum ether (80-100)
Sources & evidence
- ORD record
- ord-236d1d0d4bf144c78afaa57edb218633
- Source dataset
- uspto-grants-1976_08
- Patent number
- US03975443
Reaction notes
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