Sodium Cyanide → Dimethyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

HRID 32894

反応式

HRID 32894 の反応式
F[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[C-]#N.[Na+].CCO.[CH3:23][N:24](C=O)[CH3:25]>CCOC(C)=O>[CH3:23][N:24]([CH3:25])[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1

参加物

5

反応物 3

HCID 8929Sodium CyanideHCID 19794673N,N-dimethylformamide ethanolHCID 532567081-(5-Fluoro-2-nitrophenyl)piperidine

生成物 1

HCID 69312829Dimethyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine収率 27%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
130 °C

実験手順

To a solution of 1-(5-fluoro-2-nitro-phenyl)-piperidine (294 mg, 1.31 mmol, as prepared in the previous step) in 8 mL EtOH-DMF (v/v) was added NaCN (128 mg, 2.6 mmol). The reaction was heated to 130° C. in a sealed tube for 24 h. The reaction was diluted with EtOAc (50 mL) and washed with water (2×50 mL). Chromatography (50% EtOAc-hexane) of the crude product afforded 88 mg (27%) the title compound as well as 78 mg (24%) (1-(5-ethoxy-2-nitro-phenyl)-piperidine as yellow solids. Mass spectrum (ESI, m/z): Calcd. for C13H19N3O2, 250.1 (M+H), found 250.0.

後処理

  1. washwashed with water (2×50 mL)

出典と根拠

ORDレコード
ord-86b810c8a16945c2aa27b3ff2b97ca07
出典データセット
uspto-grants-2008_09
特許番号
US07427683B2

関連ノート

読み込み中…