Chloroacetyl chloride → 2-Chloro-1-(4-methylpiperidin-1-yl)ethan-1-one

HRID 1971848Notes

Reaction equation

HRID 1971848 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(N(CC)CC)C.[Cl:15][CH2:16][C:17](Cl)=[O:18]>C(OCC)C.ClCCl>[Cl:15][CH2:16][C:17]([N:5]1[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]1)=[O:18]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 693814-Methylpiperidine

Product 1

HCID 41169262-Chloro-1-(4-methylpiperidin-1-yl)ethan-1-one

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-Methyl-piperidine (5.00 g, 50.42 mmol) and triethylamine (7.65 g, 75.63 mmol) in ethyl ether (25 ml) was added dropwise a solution of chloroacetyl chloride (6.83 g, 60.50 mmol) in ethyl ether (30 mL). The mixture was warmed to room temperature and stirred overnight. Then the mixture was diluted with dichloromethane, washed with water, dried and concentrated in vacuo to afford the crude titled compound (crude yield 100%), which was used directly in the subsequent step reaction.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3492a2eacabd455fb68b9a13e7782b85
Source dataset
uspto-grants-2013_04
Patent number
US08431581B2

Reaction notes

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