4-Pyridinecarboxylic acid, 1-oxide → HCID 54369551, compound

HRID 1377580Notes

Reaction equation

HRID 1377580 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[C:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:22]=1.[C:23](O)(=[O:31])[C:24]1[CH:29]=[CH:28][N+:27]([O-])=[CH:26][CH:25]=1.O.[OH:34]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.P([O-])(O)(O)=O.[Na+]>C(Cl)Cl>[N:27]1[CH:28]=[CH:29][C:24]([C:23]([N+:19]2([O-:34])[CH2:18][CH2:17][C:16](=[C:15]3[C:10]4=[N:11][CH:12]=[CH:13][CH:14]=[C:9]4[CH2:8][CH2:7][C:6]4[CH:22]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]3=4)[CH2:21][CH2:20]2)=[O:31])=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 124087DesloratadineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23672064Monosodium phosphate

Product 1

HCID 54369551HCID 54369551, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 5.01 g (16.1 mmol) of 4-(8-chloro-5,6-dihydro-11 H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine, 2.19 g (15.7 mmol) of isonicotinic acid N-oxide, and 2.33 g (17.2 mmol) of 1-hydroxybenzotriazole hydrate in 30 mL of dry methylene chloride at -15° C. and under a nitrogen atmosphere was added dropwise over 25 minutes a solution of 3.26 g (16.9 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 60 mL of dry methylene chloride. The reaction mixture was slowly allowed to warm to room temperature. After 3 hours the mixture was poured into a solution of 10% aqueous sodium dihydrogen phosphate and extracted three times with methylene chloride. The combined organic portions were dried over MgSO4, filtered, and concentrated in vacuo to give a product which was purified via flash chromatography and recrystallized using isopropyl ether to give 1.35 gms (82%) of 1-(4-pyridinyl carbonyl)-4-(8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine N1 -oxide as a white solid (228° C., dec).

Workup

  1. extractionextracted three times with methylene chloride
  2. dry with materialThe combined organic portions were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a product which
  6. customwas purified via flash chromatography
  7. customrecrystallized

Sources & evidence

ORD record
ord-73bf1b4992e9484ebad31c3be873797d
Source dataset
uspto-grants-1997_09
Patent number
US05665726

Reaction notes

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