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 275278Notes

Reaction equation

HRID 275278 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

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##

Workup

  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

Sources & evidence

ORD record
ord-c6dc84e46d104623b15d54e6f9a73627
Source dataset
uspto-grants-1995_02
Patent number
US05393753

Reaction notes

Loading…