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

HRID 331081Notes

Reaction equation

HRID 331081 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

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 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

  1. temperatureThe solution was cooled
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24609cee610845f38a3cfbb85d1dae6e
Source dataset
uspto-grants-2014_11
Patent number
US08877761B2

Reaction notes

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