Methanol → HCID 20252211, compound

HRID 1284619Notes

Reaction equation

HRID 1284619 reaction equation
[OH-].[K+].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][NH2:19])[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20](=[S:22])=[S:21].[CH3:23]O>>[CH2:3]([N:10]1[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][NH:19][C:20](=[S:22])[S:21][CH3:23])[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 31492693-(4-benzylpiperazin-1-yl)propan-1-amine

Product 1

HCID 20252211HCID 20252211, compound

Procedure

To a solution of potassium hydroxide (1.3 g) in methanol (9 ml) was added 3-(4-benzyl-1-piperazinyl)propylamine (4.9 g) and thereto was added carbon disulfide (1.8 g) under ice cooling over a period of 10 minutes. The resulting mixture was stirred for 4 hours under ice cooling. The reaction mixture was evaporated under reduced pressure. The residual oil was dissolved in water (20 ml) and washed with diethyl ether. The washed aqueous layer was ice-cooled and thereto was added methyl iodide (3.0 g) with stirring under ice-cooling over a period of 10 minutes. The resulting mixture was stirred for 4 hours under ice-cooling. The reaction mixture was extracted with ethyl acetate, dried over magnesium sulfate and the evaporated under reduced pressure to give an oil of methyl N-[3-(4-benzyl-1-piperazinyl)propyl]dithiocarbamate (4.6 g).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionThe residual oil was dissolved in water (20 ml)
  3. washwashed with diethyl ether
  4. temperaturecooled
  5. additionwas added methyl iodide (3.0 g)
  6. stirringwith stirring under ice-
  7. temperaturecooling over a period of 10 minutes
  8. stirringThe resulting mixture was stirred for 4 hours under ice-
  9. temperaturecooling
  10. extractionThe reaction mixture was extracted with ethyl acetate
  11. dry with materialdried over magnesium sulfate
  12. customthe evaporated under reduced pressure

Sources & evidence

ORD record
ord-e7aa7eefcf0e474eb65b20f5bcb74003
Source dataset
uspto-grants-1986_01
Patent number
US04563524

Reaction notes

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