Chloroform → 4-(Dimethylamino)piperidine-1-carbonyl chloride

HRID 377266Notes

Reaction equation

HRID 377266 reaction equation
[Cl:1][C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[CH3:13][N:14]([CH3:21])[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C.C(Cl)(Cl)Cl>C1C=CC=CC=1>[CH3:13][N:14]([CH3:21])[CH:15]1[CH2:20][CH2:19][N:18]([C:2]([Cl:1])=[O:4])[CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 94429TriphosgeneHCID 417391N,N-Dimethylpiperidin-4-amine

Product 1

HCID 217159014-(Dimethylamino)piperidine-1-carbonyl chlorideYield 40.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

Triphosgene (1.78 g, 6 mmol) was dissolved in benzene (120 ml), followed by the addition of a solution of 4-dimethylaminopiperidine (1.96 g, 15.3 mmol) in benzene and triethylamine (1.82 g, 18 mmol). The resulting mixture was stirred overnight at room temperature. Chloroform was added to the reaction mixture, and the resulting mixture was washed with water. The organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure, and the residue was then purified by chromatography on a silica gel (chloroform-acetone mixed solvent [1:2]), whereby 4-dimethylaminopiperidinocarbonyl chloride (465 mg, 16%) was obtained.

Workup

  1. washthe resulting mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was then purified by chromatography on a silica gel (chloroform-acetone mixed solvent [1:2])

Sources & evidence

ORD record
ord-09a18f5032b041999c9f7854c29275a8
Source dataset
uspto-grants-2000_02
Patent number
US06025385

Reaction notes

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