4-Pyridinecarboxylic acid, 1-oxide → HCID 86745660, compound

HRID 1030098Notes

Reaction equation

HRID 1030098 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[CH2:7][CH2:8][C:9]3[CH2:16][CH:15]=[CH:14][CH:13]=[CH:12][C:11](=[C:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)[C:10]=3[C:2]=12.[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+:20]2([O-:34])[CH2:21][CH2:22][C:17](=[C:11]3[C:10]4[C:2]5[C:3]([CH2:7][CH2:8][C:9]=4[CH2:16][CH:15]=[CH:14][CH:13]=[CH:12]3)=[CH:4][CH:5]=[CH:6][N:1]=5)[CH2:18][CH2:19]2)=[O:31])=[CH:25][CH:26]=1

Participants

7

Reactant 5

HCID 261304-Pyridinecarboxylic acid, 1-oxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 23672064Monosodium phosphateHCID 67796845HCID 67796845, compound

Product 1

HCID 86745660HCID 86745660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 4.50 g (15.5 mmol) of 4-(5,6,7,12-tetrahydrobenzocycloocta[1,2-b]pyridin-12-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 min. 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 with methylene chloride (3x). The combined organic portions were dried over MgSO4, filtered, and concentrated in vacuo to give a product which was purified via flash chromatography to give 1-(4-pyridinyl carbonyl)-4-(5,6,7,12-tetrahydrobenzocycloocta[1,2-b]pyridin-12-ylidene)piperidine N-oxide as a colorless glass.

Workup

  1. extractionextracted with methylene chloride (3x)
  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

Sources & evidence

ORD record
ord-f9599074b1534f39a9bf0680f414efd3
Source dataset
uspto-grants-1992_04
Patent number
US05104876

Reaction notes

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