Chloroacetyl chloride → HCID 19831355, compound

HRID 1493421Notes

Reaction equation

HRID 1493421 reaction equation
[CH2:1]([NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([O:14][CH3:15])[C:8]([CH3:17])([CH3:16])[CH2:7]1)[CH2:2][CH2:3][CH3:4].[Cl:18][CH2:19][C:20](Cl)=[O:21]>ClCCl.C(OCC)C>[CH2:1]([N:5]([CH:6]1[CH2:7][C:8]([CH3:16])([CH3:17])[N:9]([O:14][CH3:15])[C:10]([CH3:13])([CH3:12])[CH2:11]1)[C:20](=[O:21])[CH2:19][Cl:18])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 21182124HCID 21182124, compound

Product 1

HCID 19831355HCID 19831355, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 48.5 g (0.200 mol) of 4-butylamino-1-methoxy-2,2,6,6-tetramethylpiperidine in 150 ml of dichloromethane is added over a one hour interval at -10° C. to a solution of 11.3 g (0.100 mol) of chloroacetyl chloride in 100 ml of dichloromethane. The reaction mixture is then stirred at ambient temperature for 1 hour. The mixture is diluted with diethyl ether (500 ml), and solids are removed by filtration. The filtrate is washed with 1N hydrochloric acid (2×75 ml) and saturated sodium bicarbonate (100 ml), then dried over magnesium sulfate and concentrated to afford 27.8 g (87% yield) of the title compound, a pale yellow oil.

Workup

  1. customare removed by filtration
  2. washThe filtrate is washed with 1N hydrochloric acid (2×75 ml) and saturated sodium bicarbonate (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e3946938d54d43a1b9d84bafe3041c81
Source dataset
uspto-grants-1991_06
Patent number
US05021478

Reaction notes

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