Water → Piperazine, 1-(chloroacetyl)-4-(2-pyrimidinyl)- (9CI)

HRID 1246225Notes

Reaction equation

HRID 1246225 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[N:6]1([C:12]2[N:17]=[CH:16][CH:15]=[CH:14][N:13]=2)[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1.C(N(CC)CC)C.O>ClCCl>[Cl:1][CH2:2][C:3]([N:9]1[CH2:10][CH2:11][N:6]([C:12]2[N:13]=[CH:14][CH:15]=[CH:16][N:17]=2)[CH2:7][CH2:8]1)=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 4149207Piperazine, 1-(chloroacetyl)-4-(2-pyrimidinyl)- (9CI)Yield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (1.16 ml, 14.62 mmol) is added to an ice-cooled solution of 2-(1-piperazinyl)pyrimidine (2.0 g, 12.18 mmol) in dichloromethane (20 ml) and triethylamine (5.09 ml, 36.54 mmol), and the mixture is stirred for 5 minutes and then warmed to room temperature. After 30 min at RT, water (50 ml) is then added to the mixture, which is extracted twice with methylene chloride (50 ml). The organic phase is washed with saturated sodium chloride solution. Drying of the organic phase over sodium sulphate, filtration, concentration under reduced pressure and silica gel chromatography (mobile phase: cyclohexane/ethyl acetate=10:1 to 1:1) gives 2.05 g (70%) of product as a colourless solid.

Workup

  1. waitAfter 30 min at RT
  2. extractionis extracted twice with methylene chloride (50 ml)
  3. washThe organic phase is washed with saturated sodium chloride solution
  4. dry with materialDrying of the organic phase over sodium sulphate, filtration, concentration under reduced pressure and silica gel chromatography (mobile phase: cyclohexane/ethyl acetate=10:1 to 1:1)

Sources & evidence

ORD record
ord-4cf8675ce4da43f88aaa56433e029c0a
Source dataset
uspto-grants-2006_10
Patent number
US07125995B2

Reaction notes

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