Phosgene → 1-Piperidinecarbonyl chloride

HRID 1249753Notes

Reaction equation

HRID 1249753 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:7](Cl)([Cl:9])=[O:8]>C(Cl)Cl>[N:1]1([C:7]([Cl:9])=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 8082Piperidine

Product 1

HCID 2420851-Piperidinecarbonyl chlorideYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Piperidine (0.3 g, 3.52 mmol) was added to a mixture of phosgene (4.7 ml of 20% phosgene in toluene solution, 8.81 mmol) in methylene chloride (5 ml) at 0° C. The mixture was stirred at 0° C. for 1 hour. The reaction mixture was evaporated in vacuo. The residue was suspended in ether, filtered and the eluents were condensed to obtain a yellow oil. Purification by flash column chromatography (silica gel, 0-20% ethyl acetate/hexane) gave 0.162 g of the title product. IR (film) 1738.9 cm−1.

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. filtrationfiltered
  3. customcondensed
  4. customto obtain a yellow oil
  5. customPurification by flash column chromatography (silica gel, 0-20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39e0029524864c4e8d6b44574e2c7449
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

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