Thionyl Chloride → 1-(3,3,3-Trifluoropropyl)piperidine-4-carbonyl chloride

Reaction equation

[F:1][C:2]([F:15])([F:14])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11](O)=[O:12])[CH2:7][CH2:6]1.S(Cl)([Cl:18])=O>>[F:1][C:2]([F:15])([F:14])[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][CH:8]([C:11]([Cl:18])=[O:12])[CH2:7][CH2:6]1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 59333911HCID 59333911, compound

Product 1

HCID 593339341-(3,3,3-Trifluoropropyl)piperidine-4-carbonyl chlorideYield 68%

Conditions

Temperature: 80 °C

Procedure

A suspension of 1-(3,3,3-trifluoropropyl)piperidine-4-carboxylic acid (4.40 g, 20.0 mmol) in thionyl chloride (20 mL) was heat to 80° C. for 15 h. The solution was cooled and concentrated in vacuo to yield a brown foam (3.0 g, 68%).

Workup

temperatureThe solution was cooled
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-bdb72e4902a94833bed3d8bce4d0de0f
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183255B2

Reaction notes

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