Water → 1-[2-Methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazine

HRID 2416667Notes

Reaction equation

HRID 2416667 reaction equation
[OH-].[Na+].FC(F)(F)C([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[C:17]([S:19]([C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)(=[O:21])=[O:20])[CH:16]=[CH:15][C:14]=2[O:32][CH3:33])[CH2:9][CH2:8]1)=O.O>CO>[CH3:33][O:32][C:14]1[CH:15]=[CH:16][C:17]([S:19]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[CH:18][C:13]=1[N:10]1[CH2:11][CH2:12][NH:7][CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 121366542,2,2-Trifluoro-1-{4-[2-methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazin-1-yl}-ethanone

Product 1

HCID 69186961-[2-Methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazineYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 6N NaOH (0.5 mL) was added to a suspension of 2,2,2-trifluoro-1-{4-[2-methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazin-1-yl}-ethanone (1) (0.110 g; 0.23 mmol ) in methanol. After stirring at 80° C. for 10 min water was added (10 ml) and the mixture was extracted into ethyl acetate (20 ml). The organic phase was dried (Na2SO4) and concentrated in vacuo to give 1-[2-methoxy-5-(naphthalene-1-sulfonyl)-phenyl]-piperazine (101) as a white solid (0.060 g , 68%), MS, MH+ 383. The hydrochloride salt was prepared from ethanol-hydrogen chloride, m. p. 154-158° C.

Workup

  1. additionwas added (10 ml)
  2. extractionthe mixture was extracted into ethyl acetate (20 ml)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7d94a0533dae4dacace73d86786df233
Source dataset
uspto-grants-2004_11
Patent number
US06825202B2

Reaction notes

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