3-Chloropropionitrile → 3-(3-Piperidinomethylbenzylthio)propionitrile

HRID 35604

Reaction equation

HRID 35604 reaction equation
Cl.Cl.[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[CH2:13][S:14][C:15](=N)N)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.ClC[CH2:23][C:24]#[N:25].[OH-].[Na+]>O.C(O)C>[N:3]1([CH2:9][C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[CH2:13][S:14][CH2:15][CH2:23][C:24]#[N:25])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 109633-ChloropropionitrileHCID 14798Sodium HydroxideHCID 212945082-(3-Piperidinomethylbenzyl)isothiourea dihydrochloride

Product 1

HCID 212945353-(3-Piperidinomethylbenzylthio)propionitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A stirred solution of the above isothiourea (1.2 g) and 3-chloropropionitrile (0.4 ml) in a mixture of water (7 ml) and ethanol (5 ml) was treated at 0°-5° C. with 2.5N sodium hydroxide (5.3 ml). The reaction mixture was stirred at 0°-5° C. for a further hour and then allowed to warm to 20° C. The reaction mixture was extracted with ethyl acetate and the extracts washed with water, dried and evaporated to provide 3-(3-piperidinomethylbenzylthio)propionitrile as an oil.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washthe extracts washed with water
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-32d906c82aa74fe0909bac945dd9dd2c
Source dataset
uspto-grants-1988_08
Patent number
US04767769

Linked notes

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