Water → 4-(3-Piperidinomethylphenylthio)butyronitrile

HRID 35605

Reaction equation

HRID 35605 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([SH:14])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH2:23][CH2:24][C:25]#[N:26].O>CN(C)C=O>[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([S:14][CH2:22][CH2:23][CH2:24][C:25]#[N:26])[CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 214124-BromobutyronitrileHCID 135055073-(Piperidin-1-ylmethyl)benzenethiol

Product 1

HCID 212945544-(3-Piperidinomethylphenylthio)butyronitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred suspension of 3-piperidinomethylthiophenol (0.36 g) in dry dimethylformamide (4 ml) was treated with anhydrous potassium carbonate (0.5 g) and stirred for 30 minutes. 4-Bromobutyronitrile (0.18 ml) was then added to the reaction mixture with dimethylformamide (1 ml) and the resultant suspension stirred at room temperature for 48 hours. The resulting product was poured into 5 volumes of water and extracted with ethyl acetate; the extracts were washed with water, dried and evaporated to give 4-(3-piperidinomethylphenylthio)butyronitrile as an orange-red oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washthe extracts were washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-f943add7633e41be847802063bf84698
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Linked notes

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