Water → Ammonia

HRID 1381869Notes

Reaction equation

HRID 1381869 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][C:7](=[O:22])[C:6]=2[CH:23]=1.[BH4-].[Na+].O>CO.C(Cl)Cl>[NH3:11].[OH:22][CH:7]1[C:6]2[CH:23]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[C:15](=[C:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)[C:10]2=[N:11][CH:12]=[CH:13][CH:14]=[C:9]2[CH2:8]1

Participants

7

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 14637769HCID 14637769, compound

Product 2

HCID 222AmmoniaHCID 146377708-Chloro-11-(piperidin-4-ylidene)-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridin-6-ol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Mix the title compound of Example 1, (0.29 g, 0.893 mmol) in CH3OH (14 mL) at 0° C. under an argon atmosphere. Add NaBH4 (165 mg, 4.36 mmol) in 3 portions. After 30 minutes, pour the mixture into water and extract (3X) with CH2Cl2. Combine the organic portions, wash once with brine, dry over sodium sulfate, filter and concentrate in vacuo to give a crude product. Purifiy via flash chromatography [5-10% CH3OH saturated with NH3 in CH2Cl2 ] to give the title compound, which can be triturated with isopropyl ether/pentane to give an off-white solid (249 mg, 85%).

Workup

  1. extractionextract (3X) with CH2Cl2
  2. washwash once with brine
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate in vacuo
  6. customto give a crude product

Sources & evidence

ORD record
ord-3e75e386e6574c859b551290e1ebfca5
Source dataset
uspto-grants-1989_02
Patent number
US04804666

Reaction notes

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