Sodium Hydroxide → HCID 53988844, compound

HRID 482280Notes

Reaction equation

HRID 482280 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([CH2:12][N:13]3[CH2:18][CH2:17][CH:16]([C:19]([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=4)([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)[OH:20])[CH2:15][CH2:14]3)=[CH:8][CH:7]=2)[CH2:3][CH2:2]1.ClC1C=C(C=CC=1)C(OO)=[O:46].[OH-].[Na+]>C(Cl)Cl>[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[CH:8][C:9]([CH2:12][N+:13]3([O-:46])[CH2:14][CH2:15][CH:16]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:23][CH:22]=4)([C:31]4[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:33][CH:32]=4)[OH:20])[CH2:17][CH2:18]3)=[CH:10][CH:11]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 11837562HCID 11837562, compound

Product 1

HCID 53988844HCID 53988844, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 10.0 grams (0.018 mole) of N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxymethyl]piperidine in methylene chloride was cooled to 0° C., and 3.1 grams (0.01 2 mole) of 50% 3-chloroperoxybenzoic acid was added in two portions. Upon completion of the addition the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 18 hours. After this time, the reaction mixture was poured into aqueous 5% sodium hydroxide solution. The organic layer was separated and washed with aqueous 5% sodium hydroxide solution. The organic layer was then filtered through phase separated silicone treated paper. The filtrate was concentrated under reduced pressure, yielding 10.2 grams of N-[4-(cyclopropylmethoxy)phenylmethyl]-4-[bis(4-trifluoromethylphenyl)hydroxy-methyl]piperidine N-oxide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. customThe organic layer was separated
  3. washwashed with aqueous 5% sodium hydroxide solution
  4. filtrationThe organic layer was then filtered through phase
  5. customseparated silicone treated paper
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-89eac9321f9f4be8bff49b44e4243d5d
Source dataset
uspto-grants-1998_08
Patent number
US05795901

Reaction notes

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