1-Benzyl-4-piperidone → 1-PIPERIDINECARBONYL CHLORIDE, 4-OXO-

HRID 550815Notes

Reaction equation

ClC(Cl)(OC(=O)[O:6][C:7]([Cl:10])(Cl)Cl)Cl.C([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)C1C=CC=CC=1>C(Cl)Cl>[O:26]=[C:23]1[CH2:24][CH2:25][N:20]([C:7]([Cl:10])=[O:6])[CH2:21][CH2:22]1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of triphosgene (2.84 g, 9.6 mmol) in methylene chloride (100 mL) at 0° C. was treated with a solution of 1-benzyl-piperidin-4-one (6.0 g, 31.7 mmol) in methylene chloride (100 mL). The reaction mixture was allowed to warm to 25° C. and was stirred at 25° C. overnight. At this time, the mixture was concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, gradient elution 60/40 ethyl acetate/hexanes) afforded 4-oxo-piperidine-1-carbonyl chloride (3.9 g, 76%) as a brown oil. The NMR spectrum obtained on the sample is compatible with its structure.

Workup

concentrationAt this time, the mixture was concentrated in vacuo
washFlash chromatography (Merck Silica gel 60, 230-400 mesh, gradient elution 60/40 ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-c97fa9e3bcfa41a69b3efcc92cfb9657
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07947692B2

Reaction notes

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