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

HRID 993411Notes

Reaction equation

HRID 993411 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-12b9277627944cb1b1667504779b9ad2
Source dataset
uspto-grants-2002_10
Patent number
US06472536B1

Reaction notes

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