Phosgene → 4-(Phenylmethyl)-1-piperidinecarbonyl chloride

HRID 1249752Notes

Reaction equation

HRID 1249752 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14](Cl)([Cl:16])=[O:15]>>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([C:14]([Cl:16])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 317384-Benzylpiperidine

Product 1

HCID 183286854-(Phenylmethyl)-1-piperidinecarbonyl chlorideYield 69.1%

Conditions

Temperature
0 °C

Procedure

4-Benzylpiperidine (0.5 g, 2.86 mmol) was added to a mixture of phosgene (3.8 ml of 20% phosgene in toluene solution, 7.13 mmol). The mixture was stirred at 0° C. for 1 hour. The reaction mixture was partitioned between water (25 ml) and ethyl acetate (2×25 ml). The organic phase was washed with 1N HCl (1×40 ml), saturated sodium chloride (1×50 ml), dried over sodium sulfate and concentrated to give a yellow oil. Purification by flash column chromatography (silica gel, 0-10% ethyl acetate/hexane) gave 0.47 g of title product. IR (film) 1733.1 cm−1.

Workup

  1. customThe reaction mixture was partitioned between water (25 ml) and ethyl acetate (2×25 ml)
  2. washThe organic phase was washed with 1N HCl (1×40 ml), saturated sodium chloride (1×50 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. customPurification by flash column chromatography (silica gel, 0-10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-89697e7229c3480ab8c8fc748ee5b287
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

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