Sodium Hydroxide → HCID 68699282, compound

HRID 2244382Notes

Reaction equation

HRID 2244382 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:33](C)[C:34](=O)C(F)(F)F)=[C:6]([CH:32]=1)[C:7]([N:9]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:31][CH2:30]2)=[CH:25][CH:24]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=1)=[O:8].[OH-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:33][CH3:34])=[C:6]([CH:32]=1)[C:7]([N:9]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]2[CH2:31][CH2:30]2)=[CH:27][CH:28]=1)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:21])[F:19])[CH:13]=1)=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86615239HCID 86615239, compound

Product 1

HCID 68699282HCID 68699282, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

35 mg of 5-chloro-N-(4-cyclopropyl-benzyl)-2-[methyl-(2,2,2-trifluoro-acetyl)-amino]-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide were dissolved in 1 ml methanol and 0.06 ml 1N aqueous NaOH and heated to 55° C. for 5 hours. The mixture was then concentrated in vacuo, diluted with ethyl acetate and washed with water and brine. The organic phase was dried over magnesium sulfate, filtered off and concentrated in vacuo, to give 28 mg (96%) 5-chloro-N-(4-cyclopropyl-benzyl)-2-methylamino-N-[2-(3-trifluoromethyl-phenyl)-ethyl]-benzamide as a light yellow viscous oil. (ISP) 503.1 (M+H)+.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additiondiluted with ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-279aa18c052846e89eef8ed9f1e49b63
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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