Thionyl Chloride → 4-Piperidinecarbonyl chloride, 1-benzoyl-

HRID 1253025Notes

Reaction equation

S(Cl)([Cl:3])=O.[C:5]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]1)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[C:5]([N:13]1[CH2:18][CH2:17][CH:16]([C:19]([Cl:3])=[O:21])[CH2:15][CH2:14]1)(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 789351-Benzoylpiperidine-4-carboxylic acid

Product 1

HCID 106822064-Piperidinecarbonyl chloride, 1-benzoyl-

Conditions

Temperature: 30 °C

Procedure

Thionyl chloride (2.0 ml, 3.3 g, 27 mmol) was added to 1-benzoyl-4-piperidinecarboxylic acid (0.31 g, 1.33 mmol) at 25° C. After stirring for 48 hours, the solution was warmed to 30° C. and concentrated under a stream of nitrogen. The 1-benzoyl-4-piperidinecarbonyl chloride, sufficiently pure for subsequent reactions, was obtained as a colorless oil which crystallized during storage at 0° C.

Workup

concentrationconcentrated under a stream of nitrogen

Sources & evidence

ORD record: ord-463827ba9bd74a9a9271a12f4ec85579
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04746669

Reaction notes

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