4-Fluoroaniline → Diisopropyl Ether

HRID 49793

Reaction equation

HRID 49793 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[OH:13]N1[C:18]2C=CC=[CH:22][C:17]=2N=N1.Cl.[CH2:24](N=C=NCCC[N:32]([CH3:34])C)C.[F:35][C:36]1[CH:42]=[CH:41][C:39](N)=[CH:38][CH:37]=1>ClCCl>[CH:17]([O:12][CH:10]([CH3:7])[CH3:24])([CH3:22])[CH3:18].[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([C:39]2[CH:41]=[CH:42][C:36]([F:35])=[CH:37][CH:38]=2)[CH2:8][CH:9]1[C:34](=[O:13])[NH2:32])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 97314-FluoroanilineHCID 757711-HydroxybenzotriazoleHCID 1172551-Acetylpiperidine-4-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 2

HCID 7914Diisopropyl EtherHCID 227418291-Acetyl-4-(4-fluorophenyl)-carbamoylpiperidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of N-acetylpiperidine-4-carboxylic acid (514 mg), 1-hydroxybenzotriazole (405 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (575 mg) and 4-fluoroaniline (284.2 ml) in dichloromethane (5 ml) was stirred for 18 hours at ambient temperature. The mixture was diluted with dichloromethane and washed with water, saturated aqueous sodium hydrogen carbonate, water, and brine. After drying with magnesium sulfate, the solvents were removed under reduced pressure. A residue was purified by column chromatography (silica gel 40 ml, dichloromethane:methanol=15:1). After trituration with diisopropyl ether, 1-acetyl-4-(4-fluorophenyl)-carbamoylpiperidine (532 mg) was obtained.

Workup

  1. washwashed with water, saturated aqueous sodium hydrogen carbonate, water, and brine
  2. dry with materialAfter drying with magnesium sulfate
  3. customthe solvents were removed under reduced pressure
  4. customA residue was purified by column chromatography (silica gel 40 ml, dichloromethane:methanol=15:1)

Sources & evidence

ORD record
ord-7d7f0fcf5281400cbfb6b320c8612b93
Source dataset
uspto-grants-2004_03
Patent number
US06710043B1

Linked notes

Loading…