Water → 2-chloro-N-[1-[2-(1H-indol-3-yl)ethyl]-4-piperidinyl]acetamide

HRID 325887Notes

Reaction equation

HRID 325887 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+].O>C(=O)([O-])[O-].[K+].[K+].ClCCl>[Cl:1][CH2:2][C:3]([NH:6][CH:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:9][CH2:8]1)=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chloride2×HCID 11430Potassium CarbonateHCID 2154154-Piperidinamine, 1-(2-(1H-indol-3-yl)ethyl)-, hydrate

Product 1

HCID 204631842-chloro-N-[1-[2-(1H-indol-3-yl)ethyl]-4-piperidinyl]acetamideYield 121.1%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (4.0 cm3, 50.18 mmol) was added dropwise to a vigorously stirred mixture of 4-amino-1-(2-[indol-3-yl]ethyl)piperidine (12.10 g, 49.8 mmol), potassium carbonate (7.0 g 50.72 mmol) water (100 cm3) and dichloromethane (300 cm3). After 3/4 hour more chloroacetyl chloride (0.5 cm3, 6.27 mmol) and potassium carbonate (0.5 g, 3.62 mmol) were added and stirring continued for a further 3/4 hour. The organic phase was separated, washed with water, dried over magnesium sulphate and evaporated to give 2-chloro-N-[1-[2-(1H-indol-3-yl)ethyl]-4-piperidinyl]acetamide (19.29 g crude)

Workup

  1. waitcontinued for a further 3/4 hour
  2. customThe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-7873a456bc2c4afc97ddce034352bd06
Source dataset
uspto-grants-1984_04
Patent number
US04443461

Reaction notes

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