4-Pyridinecarboxylic acid, 1-oxide → 4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)-piperidine N1-oxide

HRID 275278

반응식

HRID 275278 반응식
Cl.CN(C)CCCN=C=NCC.[NH:13]1[CH2:18][CH2:17][C:16](=[C:19]2[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=3[CH2:23][CH2:22][N:21]3[CH:30]=[CH:31][N:32]=[C:20]23)[CH2:15][CH2:14]1.[N+:33]1([O-])[CH:38]=[CH:37][C:36]([C:39](O)=[O:40])=[CH:35][CH:34]=1.O.[OH:44]N1C2C=CC=CC=2N=N1.C(=O)(O)[O-].[Na+]>ClCCl.O>[N:32]1[CH:31]=[CH:30][N:21]2[CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=3[C:19](=[C:16]3[CH2:15][CH2:14][N+:13]([O-:44])([C:39]([C:36]4[CH:37]=[CH:38][N:33]=[CH:34][CH:35]=4)=[O:40])[CH2:18][CH2:17]3)[C:20]=12

참가 물질

8

반응물 5

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 186124926,11-dihydro-11-(4-piperidinylidene)-5H-imidazo[2,1-b][3]benzazepine

생성물 1

HCID 867484844-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)-piperidine N1-oxide수율 71.3%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
25 °C

실험 절차

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.61 g) was added to a solution of 6,11-dihydro-11-(4-piperidylidene)-5H-imidazo[2,1-b][3]benzazepine (C, 0.52 g), pyridine-4-carboxylic acid N-oxide (0.44 g) and 1-hydroxybenzotriazole hydrate (0.43 g)in dichloromethane (20 ml) at 0°-5° C. The reaction mixture was then allowed to stir and to warm to 25° C. overnight. Water and 1 M sodium bicarbonate solution were added, and the aqueous layer was extracted with dichloromethane. Combined organic extracts were washed sequentially with water and brine, and were dried, filtered, and concentrated to give 4-(5,6-dihydro-11H-imidazo[2,1-b][3]benzazepin-11-ylidene)-1-(4-pyridinylcarbonyl)-piperidine N1 -oxide (B, 0.54 g), m.p. 155°-159° C. from carbon tetrachloride-dichloromethane. ##STR26##

후처리

  1. extractionthe aqueous layer was extracted with dichloromethane
  2. washCombined organic extracts were washed sequentially with water and brine
  3. customwere dried
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c6dc84e46d104623b15d54e6f9a73627
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05393753

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