Pyridine → Diisopropyl Ether

HRID 49790Notes

Reaction equation

HRID 49790 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.[C:17](Cl)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19].N1C=CC=C[CH:25]=1>ClCCl>[CH:17]([O:22][CH:14]([CH3:13])[CH3:9])([CH3:18])[CH3:25].[C:17]([N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:16])[C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH2:5][CH2:6]1)(=[O:22])[C:18]([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 1049PyridineHCID 62493Pivaloyl chlorideHCID 47782264-fluoro-N-(piperidin-4-yl)benzamide

Product 2

HCID 7914Diisopropyl EtherHCID 9882999N-(1-pivaloylpiperidin-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 (5 ml) were added pivaloyl chloride (0.37 ml), pyridine (0.24 ml) and N,N-dimethylaminopyridine (25 mg) at ambient temperature. After stirring for 1 day, the mixture was diluted with dichloromethane, and washed with water and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. After trituration with diisopropyl ether, N-(1-pivaloylpiperidin-4-yl)-4-fluorobenzamide (305 mg) was obtained.

Workup

  1. washwashed with water and brine
  2. dry with materialAfter drying with magnesium sulfate
  3. customthe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-101a920e66c245c88cfdf39425cedef2
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Reaction notes

Loading…