Phosgene → Ethyl 1-(chlorocarbonyl)piperidine-2-carboxylate

HRID 1995849Notes

Reaction equation

HRID 1995849 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].C(N(CC)CC)C.[C:19](Cl)([Cl:21])=[O:20]>C1C=CC=CC=1>[Cl:21][C:19]([N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH:6]1[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:20]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8471TriethylamineHCID 27517Ethyl piperidine-2-carboxylate

Product 1

HCID 13233125Ethyl 1-(chlorocarbonyl)piperidine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 2-ethoxycarbonylhexahydropyridine (5 g, 32 mmol) and triethylamine (3.2 g, 32 mmol) in 15 ml of benzene is added dropwise to phosgene, with ice-bath cooling. After the addition is complete, the mixture is allowed to warm to RT and is stirred for 2 hours. The reaction is diluted with benzene to about 150 ml, washed with water (3X), dried over sodium sulfate and stripped to give N-chlorocarbonyl-2-ethoxycarbonylhexahydropyridine.

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. washwashed with water (3X)
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-4a7e811dbf7243078666d6cd19cd9139
Source dataset
uspto-grants-1983_09
Patent number
US04406689

Reaction notes

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