Methanol → HCID 20252227, compound

HRID 325897Notes

Reaction equation

HRID 325897 reaction equation
[OH-].[K+].[CH2:3]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH2:15])[CH2:8][CH2:7]1)[CH:4]=[CH2:5].[C:16](=[S:18])=[S:17].[CH3:19]O>>[CH2:3]([N:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][CH2:14][NH:15][C:16](=[S:18])[S:17][CH3:19])[CH2:8][CH2:7]1)[CH:4]=[CH2:5]

Participants

5

Reactant 4

HCID 887MethanolHCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 202522303-[4-(Prop-2-en-1-yl)piperazin-1-yl]propan-1-amine

Product 1

HCID 20252227HCID 20252227, compound

Procedure

To a solution of potassium hydroxide (6.3 g) in methanol (40 ml) was added 3-(4-allyl-1-piperazinyl)propylamine (18.8 g) and thereto was added carbon disulfide (7.8 g) under ice cooling over a period of 10 minutes. The resulting mixture was stirred for 2 hours under ice cooling. The reaction mixture was evaporated under reduced pressure. The residual oil was dissolved in water and washed with diethyl ether. The washed aqueous layer was ice-cooled and thereto was added methyl iodide (14.6 g) with stirring. The resulting mixture was stirred for 2 hours under ice-cooling. The reaction mixture was extracted with ethyl acetate, the extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and then evaporated under reduced pressure to give an oil of methyl N-[3-(4-allyl-1-piperazinyl)propyl]dithiocarbamate (17.7 g).

Workup

  1. customThe reaction mixture was evaporated under reduced pressure
  2. dissolutionThe residual oil was dissolved in water
  3. washwashed with diethyl ether
  4. temperaturecooled
  5. additionwas added methyl iodide (14.6 g)
  6. stirringwith stirring
  7. stirringThe resulting mixture was stirred for 2 hours under ice-
  8. temperaturecooling
  9. extractionThe reaction mixture was extracted with ethyl acetate
  10. washthe extract was washed with a saturated aqueous solution of sodium chloride
  11. dry with materialdried over magnesium sulfate
  12. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-733b75671d204ea580ee60beb94e633b
Source dataset
uspto-grants-1984_04
Patent number
US04443443

Reaction notes

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