Chloroacetyl chloride → 1-(Chloroacetyl)pyrrolidine

HRID 1468007Notes

Reaction equation

HRID 1468007 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[Cl:13][CH2:14][C:15](Cl)=[O:16]>ClCCl>[Cl:13][CH2:14][C:15]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:16]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 31268Pyrrolidine

Product 1

HCID 884401-(Chloroacetyl)pyrrolidineYield 60.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of pyrrolidine (0.4 g, 5.62 mmol) in dichloromethane (4 mL), triethylamine (1.176 mL, 8.44 mmol) and chloroacetyl chloride (0.451 mL, 5.62 mmol) was added. The resulting mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with dichloromethane and washed with water. The organic layer was concentrated in vacuo and residue was purified by column chromatography to give title compound (0.5 g, 60.2%); MS: 147.10 (M+).

Workup

  1. additionwas added
  2. washwashed with water
  3. concentrationThe organic layer was concentrated in vacuo and residue
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-21e320d1614f4d2581eb573a73a15d14
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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