2,4-Difluoronitrobenzene → tert-Butyl 4-(5-Fluoro-2-nitrophenyl)piperazine-1-carboxylate

HRID 1910529ノート

反応式

HRID 1910529 の反応式
F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)C(C)C)(C)C>C(#N)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]([N+:9]([O-:11])=[O:10])=[C:2]([N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)[CH:7]=1

参加物

5

反応物 3

HCID 679672,4-DifluoronitrobenzeneHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylate

生成物 1

HCID 22272537tert-Butyl 4-(5-Fluoro-2-nitrophenyl)piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2,4-Difluoronitrobenzene (10.0 g, 62.9 mmol), t-butyl piperazine-1-carboxylate (11.7 g, 62.9 mmol) and N,N-diisopropylethylamine (8.10 g, 62.9 mmol) were stirred at room temperature in dry acetonitrile (100 mL) for 16 h. The solvent was removed by rotary evaporation and the residue was dissolved in dichloromethane and washed with water. The dichloromethane was removed by rotary evaporation to collect the title compound (19.0 g, 93%). 1H NMR (400 MHz, CDCl3): δ 7.91 (dd, 1H), 6.75 (m, 2H), 3.60 (m, 4H), 3.03 (m, 4H), 1.48 (s, 9H); MS (ESI) m/z: Calculated for C15H20FN3O4: 325.14; Observed: 348.1 (M++Na).

後処理

  1. customThe solvent was removed by rotary evaporation
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with water
  4. customThe dichloromethane was removed by rotary evaporation
  5. customto collect the title compound (19.0 g, 93%)

出典と根拠

ORDレコード
ord-e2d620e81f9e419daa68187a695db843
出典データセット
uspto-grants-2013_12
特許番号
US08604021B2

反応ノート

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