Hydrochloric Acid → 2-(1-Biphenyl-4-yl-ethylamino)-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

HRID 1178160Notes

Reaction equation

HRID 1178160 reaction equation
C(OC(=O)[N:7]([CH:30]([C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:34][CH:33]=1)[CH3:31])[CH2:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17](=[O:29])[C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[C:25]([F:28])([F:27])[F:26])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.[ClH:45]>O1CCOCC1>[ClH:45].[C:35]1([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[CH:34]=[CH:33][C:32]([CH:30]([NH:7][CH2:8][C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17](=[O:29])[C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[C:25]([F:28])([F:27])[F:26])[CH2:15][CH2:16]2)=[O:10])[CH3:31])=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59559575(1-Biphenyl-4-yl-ethyl)-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 669531912-(1-Biphenyl-4-yl-ethylamino)-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochlorideYield 78.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (1-biphenyl-4-yl-ethyl)-{2-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester (140 mg, 0.23 mmol in dioxane.HCl (10 ml) was stirred at room temperature for 1 hr. The reaction mixture was concentrated to get the residue. The residue was washed with hexane to afford 98 mg (78.4% Yield) of 2-(1-Biphenyl-4-yl-ethylamino)-1-[4-(5-fluoro-2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride. LCMS Purity: 93.9%. 1H NMR (CDCl3): δ 9.6 (d, 3H), 8.0 (t, 1H), 7.8-7.6 (m, 6H), 7.6-7.36 (m, 5H), 4.5 (t, 1H), 4.2-3.6 (m, 2H), 3.6-3.4 (m, 5H), 3.2-3.0 (m, 3H), 1.6 (t, 3H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto get the residue
  3. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-cd23f59623c948c38611f3f901ab1041
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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