Pyridine → HCID 54549977, compound

HRID 1377576Notes

Reaction equation

HRID 1377576 reaction equation
[OH:1][CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[C:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)[C:5]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:4]=2[CH2:3]1.N1C=CC=CC=1.[C:30](OC(=O)C)(=[O:32])[CH3:31].[OH-].[Na+]>O.C(Cl)Cl.CO>[OH:1][CH:2]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[C:6](=[C:13]2[CH2:18][CH2:17][N:16]([C:30](=[O:32])[CH3:31])[CH2:15][CH2:14]2)[C:5]2[CH:19]=[CH:20][C:21]([Cl:23])=[CH:22][C:4]=2[CH2:3]1

Participants

8

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 146377758-Chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-ol

Product 1

HCID 54549977HCID 54549977, compoundYield 84.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 32.6 mg (0.10 mmole) of 5-hydroxy-8-chloro-11-(4-piperidylidene)-6,11-dihydro-5 H-benzo[5,6]cyclohepta[1,2-b]pyridine and 9.7)l (0.12 mmole) of pyridine in a solution of 2 mL of methanol and 1 mL of CH2Cl2 at 0° C. and under a nitrogen atmosphere was added 11.3) l (0.12 mmole) of acetic anhydride. After 30 min. the mixture was poured into water which was subsequently adjusted to pH of about 9 with aqueous sodium hydroxide. The mixture was extracted 2× with CH2Cl2. The organic portions were combined, washed once with brine, dried over Na2SO4, filtered, and concentrated in vacuo to yield 31.2 mg of the title compound as a glass.

Workup

  1. extractionThe mixture was extracted 2× with CH2Cl2
  2. washwashed once with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29c07ddea525475990bfdcd6965615ff
Source dataset
uspto-grants-1997_09
Patent number
US05665726

Reaction notes

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