Methanol → methyl N-[3-(4-phenyl-1-piperazinyl)propyl]dithiocarbamate
Reaction equation
[OH-].[K+].[C:3]1([N:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:19](=[S:21])=[S:20].[CH3:22]O>>[C:3]1([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][NH:18][C:19](=[S:21])[S:20][CH3:22])[CH2:13][CH2:14]2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
Procedure
To a solution of potassium hydroxide (2.85 g) in methanol (25 ml) was added 3-(4-phenyl-1-piperazinyl)propylamine (11.1 g) and thereto was added carbon disulfide (3.85 g) under ice cooling over a period of 10 minutes. The resulting mixture was stirred for 3 hours under ice cooling. The reaction mixture was evaporated under reduced pressure. The residual oil was dissolved in water (40 ml) and washed with diethyl ether. The washed aqueous layer was ice-cooled and thereto was added methyl iodide (7.2 g) with stirring. The resulting mixture was stirred for 2 hours under ice-cooling and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate and then evaporated to give methyl N-[3-(4-phenyl-1-piperazinyl)propyl]dithiocarbamate (12.9 g), mp 75° to 79° C.
Workup
- customThe reaction mixture was evaporated under reduced pressure
- dissolutionThe residual oil was dissolved in water (40 ml)
- washwashed with diethyl ether
- temperaturecooled
- additionwas added methyl iodide (7.2 g)
- stirringwith stirring
- stirringThe resulting mixture was stirred for 2 hours under ice-
- temperaturecooling
- extractionextracted with ethyl acetate
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-e65b8f4cf2294823bf1f928155d2de47
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04563524
Reaction notes
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