Dimethylformamide → 1-Cyclopropylpiperidine-4-carbonyl chloride
Reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.CN(C)C=O.C(Cl)(=O)C([Cl:21])=O>ClCCl>[CH:1]1([N:4]2[CH2:9][CH2:8][CH:7]([C:10]([Cl:21])=[O:12])[CH2:6][CH2:5]2)[CH2:3][CH2:2]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred mixture of 1-cyclopropyl piperidine-4-carboxylic acid (10.0 grams, 48.6 mmol, obtained in above step) in dichloromethane (198 mL) cooled at 0° C. was added dry dimethyl formamide (2 mL) followed by drop wise addition of oxalyl chloride (12.5 mL, 145.8 mmol). The reaction mixture was gradually warmed to room temperature and stirred for 1 hour. The volatiles were removed under reduced pressure and the crude 1-cyclopropyl piperidine-4-carbonyl chloride (11.0 grams). This crude product was used in the next reaction without purification.
Workup
- temperatureThe reaction mixture was gradually warmed to room temperature
- customThe volatiles were removed under reduced pressure
- customThis crude product was used in the next reaction without purification
Sources & evidence
- ORD record
- ord-bbe0d73af82945a4809fddec6b1d506f
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079894B2
Reaction notes
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