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

HRID 1381870Notes

Reaction equation

HRID 1381870 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 the title compound of Example 6 (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 (3X) 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 (3X) 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-51f243c345584523a61550a31c1c7a6c
Source dataset
uspto-grants-1989_02
Patent number
US04804666

Reaction notes

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