Chloroacetyl chloride → Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylate

HRID 1971840Notes

Reaction equation

HRID 1971840 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:25](=[O:26])[CH2:24][Cl:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 15829156Tert-butyl 4-(2-chloroacetyl)piperazine-1-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Piperazine-1-carboxylic acid tert-butyl ester (3.0 g, 16.1 mmol) and DIPEA (3.1 ml, 18.0 mmol) were dissolved in DCM (32 ml) and cooled in ice bath. To the above stirred mixture was added a solution of chloroacetyl chloride (1.33 ml, 16.7 mmol) at 0° C. Three hours later, the mixture was washed with water, dried and evaporated under reduced pressure. The residue was purified by column chromatography using EA/PE (4/1) as eluent to afford the title compound (3.3 g, yield 78.0%).

Workup

  1. temperaturecooled in ice bath
  2. washThree hours later, the mixture was washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-fc146c13c4bb4c81a36b35ad43655081
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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