Cyclopropanecarboxylic acid → N-(1-cyclopropylcarbonylpiperidin-4-yl)-4-fluorobenzamide

HRID 49791

Reaction equation

HRID 49791 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH2:3][CH2:2]1.[CH:17]1([C:20](O)=[O:21])[CH2:19][CH2:18]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH:17]1([C:20]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:16])[C:9]3[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=3)[CH2:5][CH2:6]2)=[O:21])[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 15655Cyclopropanecarboxylic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 47782264-fluoro-N-(piperidin-4-yl)benzamide

Product 1

HCID 9926015N-(1-cyclopropylcarbonylpiperidin-4-yl)-4-fluorobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of N-(piperidin-4-yl)-4-fluorobenzamide (556 mg) in dichloromethane (6 ml) were added cyclopropanecarboxylic acid (0.20 ml), 1-hydroxybenzotriazole (338 mg) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (480 mg) at ambient temperature. After stirring for 21 hours, the mixture was diluted with dichloromethane, and washed with water, saturated aqueous sodium hydrogen carbonate, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. After crystallization from diisopropyl ether, N-(1-cyclopropylcarbonylpiperidin-4-yl)-4-fluorobenzamide (627 mg) was obtained.

Workup

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate, and brine
  2. dry with materialAfter drying with magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customAfter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-172de2d3a4fd4dff8daa387af3ff6796
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Linked notes

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