Ammonium Hydroxide → 8-Chloro-11-(4-benzyl-1-piperazinyl)-dibenz[b,f][1,4]oxazepine

HRID 1450183

반응식

HRID 1450183 반응식
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9](=O)[NH:10][C:4]=2[CH:3]=1.[CH2:18]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[NH4+]>C1(C)C=CC=CC=1.Cl[Ti](Cl)(Cl)Cl>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[O:6][C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[C:9]([N:28]3[CH2:29][CH2:30][N:25]([CH2:18][C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH2:26][CH2:27]3)=[N:10][C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 14923Ammonium HydroxideHCID 759941-BenzylpiperazineHCID 766192-Chlorodibenz(b,f)-1,4-oxazepin-11(10H)-one

생성물 1

HCID 98874518-Chloro-11-(4-benzyl-1-piperazinyl)-dibenz[b,f][1,4]oxazepine수율 95.6%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 1140Toluene용매

실험 절차

To a stirred solution of 8-chloro-10,11-dihydro-dibenz[b,f][1,4]oxazepin-11-one (0.3 g; 1.22 mmol) in dry toluene (10 mL) at room temperature was added 1-benzyl piperazine (1.0 mL; 5.61 mmol; Aldrich) followed by the dropwise addition of TiCl4 (1M in toluene, 1.47 mL; 1.47 mmol). The reaction mixture was refluxed for 2 hours, cooled to room temperature and then poured into an ammonium hydroxide solution (30%, 50 mL). The resulting mixture was extracted with dichloromethane (4×50 mL), and the combined organic phases were then dried (K2CO3) and concentrated. Purification of the product was conducted on silica gel using ethyl acetate:hexane (5:1→4:1) as the eluant to give 0.471 g (95%) of the title compound as a yellow solid; m.p. 50°-52° C.

후처리

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. extractionThe resulting mixture was extracted with dichloromethane (4×50 mL)
  3. dry with materialthe combined organic phases were then dried (K2CO3)
  4. concentrationconcentrated
  5. customPurification of the product

출처 및 근거

ORD 기록
ord-5670831b8985425885dfe469db6ea6a7
출처 데이터셋
uspto-grants-1997_02
특허 번호
US05602120

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