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

HRID 1450184노트

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HRID 1450184 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0875813a71c4db8a298e0f89d0c3e74
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602120

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