Dimethylformamide → 1-Benzyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,2]benzoxazepin-2-one

HRID 981928노트

반응식

HRID 981928 반응식
N1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4]CC1=O)[CH2:12][CH2:11][CH2:10][CH2:9]3.[CH3:20][C:21](C)([O-:23])C.[K+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C[N:35](C)C=O>O>[CH2:26]([CH:20]1[C:7]2=[C:8]3[C:13](=[N:14][C:15]4=[CH:16][CH:17]=[CH:18][C:5](=[C:6]24)[O:4][NH:35][C:21]1=[O:23])[CH2:12][CH2:11][CH2:10][CH2:9]3)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 9795016HCID 9795016, 화합물HCID 23665647Potassium tert-butoxide

생성물 1

HCID 200686091-Benzyl-1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,2]benzoxazepin-2-one수율 41%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a suspension of 1,3,9,10,11,12-hexahydro-2H-quino[4,3,2-ef][1,4]benzoxazepin-2-one (4.30 g) in dry dimethylformamide (50 ml) was added potassium tert-butoxide (2.1 g). To the solution was added benzyl bromide (2.22 ml), and stirring was continued for five mins. The reaction mixture was diluted with water (150 ml) and extracted with diethyl ether. The organic phase was washed with water, brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. Trituration of the residue with pentane followed by recrystallization from methanol gave 2.42 g (41%) of product, mp 166°-167.5° C.

후처리

  1. extractionextracted with diethyl ether
  2. washThe organic phase was washed with water, brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customTrituration of the residue with pentane followed by recrystallization from methanol

출처 및 근거

ORD 기록
ord-52eddcb74c254b0784d88f87ed38dc13
출처 데이터셋
uspto-grants-1991_02
특허 번호
US04994452

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