Sodium Hydroxide → 9-Bromo-6-(4-n-propyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo-[3,2,1-jk][1,4]benzodiazepine

HRID 4069

반응식

HRID 4069 반응식
[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH2:17][CH2:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9](=O)[NH:10][C:4]=2[CH:3]=1.[CH2:20]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH2:21][CH3:22].[OH-].[Na+]>[Ti](Cl)(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]3[CH2:17][CH2:16][C:15]4[C:7]3=[C:8]([CH:12]=[CH:13][CH:14]=4)[C:9]([N:26]3[CH2:27][CH2:28][N:23]([CH2:20][CH2:21][CH3:22])[CH2:24][CH2:25]3)=[N:10][C:4]=2[CH:3]=1

참가 물질

6

반응물 3

HCID 14798Sodium HydroxideHCID 415812Piperazine, 1-propyl-, hydrochloride (1:2)HCID 138232839-Bromo-1,2dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepine-6-one

생성물 1

HCID 138232989-Bromo-6-(4-n-propyl-1-piperazinyl)-1,2-dihydrobenzo[b]pyrrolo-[3,2,1-jk][1,4]benzodiazepine수율 30.1%

시약·촉매·용매 2

HCID 24193Titanium Tetrachloride촉매HCID 1140Toluene용매

실험 절차

A stirred mixture of 7.88 g (0.0250 mole) of 9-bromo-1,2-dihydrobenzo[b]pyrrolo[3,2,1-jk][1,4]benzodiazepin-6-one and 1200 ml of toluene was heated until a solution resulted. Then there was added 32.1 g (0.25 mole) of N-propylpiperazine, followed by 14.2 g (0.075 mole) of titanium tetrachloride. The mixture was refluxed for 3 hours, and then cooled to room temperature. The mixture was stirred with 500 ml of 2N sodium hydroxide solution for 15 minutes and the layers were separated. The aqueous phase was extracted with 300 ml of toluene. The toluene layers were combined, filtered, washed once with 2N sodium hydroxide solution, twice with water, dried over anhydrous sodium sulfate, and concentrated to an oily solid. The oily solid was dissolved in 25 ml of hot ethyl acetate, filtered, and allowed to crystallize first at room temperature, then at 0° C. to yield 3.20 g (30%) of product, mp 134°-136° C.

후처리

  1. temperaturewas heated until a solution
  2. customresulted
  3. temperatureThe mixture was refluxed for 3 hours
  4. customthe layers were separated
  5. extractionThe aqueous phase was extracted with 300 ml of toluene
  6. filtrationfiltered
  7. washwashed once with 2N sodium hydroxide solution, twice with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated to an oily solid
  10. dissolutionThe oily solid was dissolved in 25 ml of hot ethyl acetate
  11. filtrationfiltered
  12. customto crystallize first at room temperature

출처 및 근거

ORD 기록
ord-e14a8dbd106648d2905843dffce31170
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723003

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