Diisopropylethylamine → t-Butyl 4-(3-(1-phenylethylamino)-4-(2,2,2-trifluoroacetyl) phenyl)piperazine-1-carboxylate

HRID 2425983Notes

Reaction equation

HRID 2425983 reaction equation
[C:1]1([CH:7]([NH:9][C:10]2[CH:15]=[C:14](F)[CH:13]=[CH:12][C:11]=2[C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:23]1([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C(N(CC)C(C)C)(C)C>C(#N)C>[C:1]1([CH:7]([NH:9][C:10]2[CH:15]=[C:14]([N:26]3[CH2:25][CH2:24][N:23]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:28][CH2:27]3)[CH:13]=[CH:12][C:11]=2[C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 587072761-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone

Product 1

HCID 58707346t-Butyl 4-(3-(1-phenylethylamino)-4-(2,2,2-trifluoroacetyl) phenyl)piperazine-1-carboxylateYield 30.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-(1-Phenylethylamino)-4-fluorophenyl)-2,2,2-trifluoroethanone (150 mg, 0.48 mmol), t-butyl piperazine-1-carboxylate (98.7 mg, 0.53 mmol), N,N-diisopropylethylamine (124 mg, 0.96 mmol) were stirred at 80° C. in dry acetonitrile (25 mL) for 21 h. The solvent was evaporated and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was evaporated and the crude compound was purified by silica chromatography using 25% ethyl acetate in hexanes to afford the title compound (70 mg, 30% yield). 1H NMR (400 MHz, CDCl3): δ 9.36 (d, 1H), 7.60 (d, 1H), 7.32 (m, 4H), 7.24 (m, 1H), 6.13 (d, 1H), 5.61 (s, 1H), 4.55 (m, 1H), 3.41 (m, 4H), 3.25 (m, 2H), 3.14 (m, 2H), 1.61 (d, 3H), 1.46 (s, 9H); MS (ESI) m/z: Calculated for C25H30F3N3O3: 477.22; Observed: 500.3 (M++Na).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was evaporated
  5. customthe crude compound was purified by silica chromatography

Sources & evidence

ORD record
ord-b755a7acf28648a69080773f1f1560c4
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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