Chloroacetyl chloride → 1-(Chloroacetyl)pyrrolidine

HRID 1383822Notes

Reaction equation

HRID 1383822 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 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of pyrrolidine (5 g, 0.07 mol) in dichloromethane (100 ml) at 0° C. was added triethylamine (11.8 ml, 0.084 mol) followed by dropwise addition of chloroacetyl chloride (6.2 ml 0.077 mol) in dichoromethane (20 ml), stirred for 2 hrs, left to warm to room temperature. The reaction was washed with water (2×100 ml), brine (1×100 ml), the organic layers were dried (MgSO4), filtered and evaporated to give the required product (9.8 g) which was used without purification.

Workup

  1. waitleft
  2. washThe reaction was washed with water (2×100 ml), brine (1×100 ml)
  3. dry with materialthe organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-1dd0fb7166a544eab1bfc8e1896bc040
Source dataset
uspto-grants-2001_07
Patent number
US06255305B1

Reaction notes

Loading…