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

反応式

HRID 275278 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

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##

後処理

  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

出典と根拠

ORDレコード
ord-c6dc84e46d104623b15d54e6f9a73627
出典データセット
uspto-grants-1995_02
特許番号
US05393753

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