Sodium hydride → 11-[4-(2-Cyanobenzyl)-1-piperazinyl]dibenz[b,f][1,4]oxazepine

HRID 1450184ノート

反応式

HRID 1450184 の反応式
[N:1]1([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:25][C:26]1[C:27]([C:32]#[N:33])=[CH:28][CH:29]=[CH:30][CH:31]=1>CN(C=O)C>[C:32]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][C:10]3[CH:18]=[CH:19][CH:20]=[CH:21][C:9]=3[N:8]=2)[CH2:6][CH2:5]1)#[N:33]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 895992-(Bromomethyl)benzonitrileHCID 706187411-(Piperazin-1-yl)dibenzo(b,f)(1,4)oxazepine

生成物 1

HCID 1897134211-[4-(2-Cyanobenzyl)-1-piperazinyl]dibenz[b,f][1,4]oxazepine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine (2.79 g, 10.0 mmol) (prepared from 10,11-dihydrodebenz[b,f][1,4]oxazepine-11-one, Aldrich and piperazine, as in example 1) in DMF (25 mL) was added sodium hydride (0.56 g, 60% in oil, 14 mmol) at 0° C. under argon. The mixture was stirred at 0° C. for 10 minutes at room temperature for 20 minutes, and then treated with α-bromo-o-tolunitrile (2.35 g, 12.0 mmol, Aldrich). The resulting mixture was stirred at room temperature overnight and quenched with saturated ammonium chloride solution (25 mL). The mixture was separated and extracted with ethyl acetate (3×50 mL). The combined organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo to dryness and the residue was subjected to column chromatography using ethyl acetate:hexane (1:2) as the eluent. The title compound was obtained as a white solid (2.34 g, 59%), m.p. 136°-138° C.; MS 395 (M+ +1).

後処理

  1. stirringThe resulting mixture was stirred at room temperature overnight
  2. customquenched with saturated ammonium chloride solution (25 mL)
  3. customThe mixture was separated
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined organic phase was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo to dryness

出典と根拠

ORDレコード
ord-f0875813a71c4db8a298e0f89d0c3e74
出典データセット
uspto-grants-1997_02
特許番号
US05602120

反応ノート

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