Ethyl Acetate → 5-Chloro-4-{4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinyl}-2-(methyloxy)aniline

HRID 419431ノート

反応式

HRID 419431 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[N:13]1[CH2:18][CH2:17][CH:16]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][F:27])[CH2:21][CH2:20]2)[CH2:15][CH2:14]1.CCOC(C)=O>CCO.[Pt]>[Cl:1][C:2]1[C:3]([N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][F:27])[CH2:23][CH2:24]3)[CH2:15][CH2:14]2)=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:7]=1)[NH2:8]

参加物

5

反応物 2

HCID 8857Ethyl AcetateHCID 594527481-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazine

生成物 1

HCID 594529605-Chloro-4-{4-[4-(2-fluoroethyl)-1-piperazinyl]-1-piperidinyl}-2-(methyloxy)aniline

試薬・触媒・溶媒 2

HCID 23939Platinum触媒HCID 702Ethanol溶媒

実験手順

1-{1-[2-Chloro-5-(methyloxy)-4-nitrophenyl]-4-piperidinyl}-4-(2-fluoroethyl)piperazine (0.370 g, 0.923 mmol) was taken up in EtOH (50 mL) and EtOAc was added to help with solubility. The catalyst, 5% sulfided platinum on carbon (150 mg) was added. The reaction was placed on a Fischer-Porter Hydrogenator under 50 psi of H2 gas and was allowed to stir at rt overnight. The catalyst was filtered off and the filtrate was concentrated in vacuo to give the title compound of step F without further purification (0.300 g, 88%). 1H NMR (400 MHz, DMSO-d6) δ ppm 6.62 (d, J=7.0 Hz, 2H), 4.51-4.79 (m, 3H), 4.37-4.51 (m, 1H), 3.73 (s, 3H), 2.95-3.21 (m, 2H), 2.20-2.80 (m, 13H), 1.72-1.85 (m, 2H), 1.37-1.61 (m, 2H).

後処理

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-91c8f8d5da5f4a60aee8d817391919e2
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

読み込み中…