Methanol → methyl N-[3-(4-isopropyl-1-piperazinyl)propyl]dithiocarbamate
Reaction equation
[OH-].[K+].[CH:3]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH2:7]1)([CH3:5])[CH3:4].[C:16](=[S:18])=[S:17].[CH3:19]O>>[CH:3]([N:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][CH2:14][NH:15][C:16](=[S:18])[S:17][CH3:19])[CH2:10][CH2:11]1)([CH3:5])[CH3:4]Participants
Procedure
To a solution of potassium hydroxide (4.9 g) in methanol (40 ml) was added 3-(4-isopropyl-1-piperazinyl)propylamine (14.7 g) and thereto was added carbon disulfide (6.0 g) under ice cooling over a period of 20 minutes. The resulting mixture was stirred for 3.5 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 (11.3 g) with stirring over a period of about 5 minutes. The resulting mixture was stirred for 2 hours under ice-cooling extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and then evaporated to give an oil of methyl N-[3-(4-isopropyl-1-piperazinyl)propyl]dithiocarbamate (15.6 g).
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 (11.3 g)
- stirringwith stirring over a period of about 5 minutes
- stirringThe resulting mixture was stirred for 2 hours under ice-
- temperaturecooling
- extractionextracted with chloroform
- washThe extract was washed with water
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-ee313229b9e143e381a7ccb5a9d71667
- Source dataset
- uspto-grants-1986_01
- Patent number
- US04563524
Reaction notes
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