Lithium Hydroxide → 4-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenylamine

HRID 634836Notes

Reaction equation

HRID 634836 reaction equation
FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH2:15][CH2:14]2)=[CH:8][CH:7]=1)=O.[OH-].[Li+]>CO.O>[C:22]1([S:19]([N:16]2[CH2:17][CH2:18][CH:13]([CH2:12][C:9]3[CH:8]=[CH:7][C:6]([NH2:5])=[CH:11][CH:10]=3)[CH2:14][CH2:15]2)(=[O:20])=[O:21])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 218770242,2,2-trifluoro-N-(4-(1-benzenesulfonyl-piperidin-4-ylmethyl)-phenyl]acetamide

Product 1

HCID 218770334-(1-Benzenesulfonylpiperidin-4-ylmethyl)-phenylamineYield 83.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 2,2,2-trifluoro-N-[4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenyl]acetamide (0.45 g) and lithium hydroxide (0.23 g) in methanol (10 mL) and water (1 mL) was stirred for about 48 hours. The reaction mixture was concentrated in vacuo, diluted with cold water, and extracted with dichloromethane. The organic layer was washed with cold water and brine, dried, and solvents removed in vacuo. The residue was crystallized from ethyl acetate/hexanes to give 4-(1-benzenesulfonylpiperidin-4-ylmethyl)-phenylamine (0.29 g, 83%), m.p. 158° C.; Analysis for C18H22N2O2S: Calc.: C, 65.43; H, 6.71; N, 8.48; Found: C, 65.59; H, 6.61; N, 8.66.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with cold water
  3. extractionextracted with dichloromethane
  4. washThe organic layer was washed with cold water and brine
  5. customdried
  6. customsolvents removed in vacuo
  7. customThe residue was crystallized from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6f2fa46d810c4210bf5bdfb0a6d5389c
Source dataset
uspto-grants-2001_02
Patent number
US06184242B2

Reaction notes

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