Diisopropylethylamine → t-Butyl 4-(5-(3,5-dichlorobenzylamino)-2-nitrophenyl)piperazine-1-carboxylate

HRID 2426084Notes

Reaction equation

HRID 2426084 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=1)[CH2:28][NH2:29].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([Cl:33])[CH:32]=1)[CH2:28][NH:29][C:2]1[CH:3]=[CH:4][C:5]([N+:21]([O-:23])=[O:22])=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 457602Benzenemethanamine, 3,5-dichloro-HCID 22272537tert-Butyl 4-(5-Fluoro-2-nitrophenyl)piperazine-1-carboxylate

Product 1

HCID 58707297t-Butyl 4-(5-(3,5-dichlorobenzylamino)-2-nitrophenyl)piperazine-1-carboxylateYield 41%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

t-Butyl 4-(5-fluoro-2-nitrophenyl)piperazine-1-carboxylate (1.3 mmol), 3,5-dichlorobenzylamine (1.3 mmol), N,N-diisopropylethylamine (1.3 mmol) were stirred at 80° C. in dry acetonitrile (25 mL) for 72 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 (41%). 1H NMR (400 MHz, CDCl3): δ 9.38 (br, 1H), 7.67 (d, 1H), 7.31 (s, 1H), 7.21 (s, 2H), 6.13 (dd, 1H), 5.70 (d, 1H), 4.42 (d, 2H), 3.54 (m, 4H), 3.38 (m, 4H), 1.49 (s, 9 H). MS (ESI) m/z: Calculated: 481.37; Observed: 482.6 (M+H+).

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-586a0263beb449dfa3bba5d77f53c8f9
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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