Water → 8-Chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-ol

HRID 1534586Notes

Reaction equation

HRID 1534586 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[C:8](=[O:22])[CH2:7][C:6]=2[CH:23]=1.[BH4-].[Na+].O>CO>[OH:22][CH:8]1[C:9]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[C:15](=[C:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:23][C:6]=2[CH2:7]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 14637773HCID 14637773, compound

Product 1

HCID 146377758-Chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-olYield 87.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mix 8-Chloro-11-(4-piperidylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-5-one (400 mg, 1.23 mmol) in CH3OH (20 mL) at 0° C. under an argon atmosphere, and add in 3 portions NaBH4 (total 231 mg, 6.10 mmol). After 30 minutes, pour the mixture into water and extract (3×) with ethyl acetate. Combine the organic portions, wash with brine, dry over sodium sulfate, filter and concentrate in vacuo. Triturate the solid with isopropyl ether/ethyl acetate to give the title compound as a white solid (351 mg, 87%).

Workup

  1. extractionextract (3×) with ethyl acetate
  2. washwash with brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customTriturate the solid with isopropyl ether/ethyl acetate

Sources & evidence

ORD record
ord-1d160101dfed4345844c2d4684724fc5
Source dataset
uspto-grants-1992_02
Patent number
US05089496

Reaction notes

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