Hydroxyamine hydrochloride → 4-[(2-Fluoro-5-trifluoromethyl-phenyl)-hydroxyiminomethyl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1986933

Reaction equation

HRID 1986933 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[F:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:28][OH:29]>N1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([C:15]2[CH:20]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:17][C:16]=2[F:25])=[N:28][OH:29])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 588175444-(2-Fluoro-5-trifluoromethyl-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 724345474-[(2-Fluoro-5-trifluoromethyl-phenyl)-hydroxyiminomethyl]-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 4-(2-fluoro-5-trifluromethyl-benzoyl)-piperidine-1-carboxylic acid tert-butyl ester (5 g, 0.013M) in pyridine (25 mL) was treated with hydroxylamine hydrochloride (1.11 g, 0.015 M -1.2 eq). The reaction was stirred under N2 at room temperature for 14 hours and then poured onto ice water (250 mL). The mixture was stirred at 0° C. for 1 hour, the product was then filtered off, washed with cold water (3×15 mL) and dried in a vacuum oven at 50° C. A white solid was obtained (5.03 g, 97%).

Workup

  1. additionpoured onto ice water (250 mL)
  2. stirringThe mixture was stirred at 0° C. for 1 hour
  3. filtrationthe product was then filtered off
  4. washwashed with cold water (3×15 mL)
  5. customdried in a vacuum oven at 50° C
  6. customA white solid was obtained (5.03 g, 97%)

Sources & evidence

ORD record
ord-96f9601b9fa54694b922c04ac4a7e486
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Linked notes

Loading…