Phosgene → 1-Acetyl-2,2,6,6-tetramethyl-4-chlorocarbonyloxypiperidine Hydrochloride

HRID 847267Notes

Reaction equation

[C:1]([N:4]1[C:9]([CH3:11])([CH3:10])[CH2:8][CH:7]([OH:12])[CH2:6][C:5]1([CH3:14])[CH3:13])(=[O:3])[CH3:2].[C:15]([Cl:18])([Cl:17])=[O:16]>C(C(C)=O)C>[ClH:17].[C:1]([N:4]1[C:5]([CH3:14])([CH3:13])[CH2:6][CH:7]([O:12][C:15]([Cl:18])=[O:16])[CH2:8][C:9]1([CH3:11])[CH3:10])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 19.9 grams (0.1 mol) of 1-acetyl-2,2,6,6-tetramethyl-4-hydroxypiperidine in 150 ml of dry methyl ethyl ketone is added dropwise at 0° C. over a 30-minute period to a solution of 28 ml (approximately 0.4 mol) of phosgene in 150 ml of methyl ethyl ketone. The reaction mixture is stirred at 0° C. for one hour, then at 20° C. for eighteen hours. Excess dissolved phosgene is flushed out into an absorption trap with a stream of nitrogen. The solid precipitate is removed by filtration, washed twice with methyl ethyl ketone and dried with suction to yield 13.7 grams (52% yield) of the title compound which melts at 113°-114° C.

Workup

waitat 20° C. for eighteen hours
customis flushed out into an absorption trap with a stream of nitrogen
customThe solid precipitate is removed by filtration
washwashed twice with methyl ethyl ketone
customdried with suction

Sources & evidence

ORD record: ord-97ba5a23aea04ff199419d877506d9ae
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05140081

Reaction notes

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