Methanol → HCID 23285058, compound

HRID 369188Notes

Reaction equation

HRID 369188 reaction equation
B(Br)(Br)Br.[CH3:5][N:6]([CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:35])[C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)=[C:24]([O:33]C)[CH:23]=2)[CH2:17][CH2:16]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.CO.[OH-].[Na+].[Cl:40]CCl>C(Cl)(Cl)Cl>[ClH:40].[CH3:5][N:6]([CH:15]1[CH2:20][CH2:19][N:18]([C:21](=[O:35])[C:22]2[CH:27]=[CH:26][C:25]([N:28]3[CH:32]=[N:31][CH:30]=[N:29]3)=[C:24]([OH:33])[CH:23]=2)[CH2:17][CH2:16]1)[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 887MethanolHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 23284900HCID 23284900, compound

Product 1

HCID 23285058HCID 23285058, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
-30 °C

Procedure

24 ml of a 1 N solution of boron tribromide in dichloromethane was dropwise added, at -40° C., to a solution of 1.0 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-[3-methoxy-4-(1,2,4-triazol-1-yl)benzoyl]piperidine in 20 ml of chloroform. The mixture was stirred overnight at that temperature and then returned to room temperature. The mixture was cooled to -30° C. and 10 ml of methanol was dropwise added thereto. The mixture was poured into ice water. The resulting mixture was made basic with a 25% aqueous sodium hydroxide solution and stirred for a while. The organic layer was separated, water-washed, and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=50/1 to 9/1) and then converted into a hydrochloride to obtain 0.42 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-[3-hydroxy-4-(1,2,4-triazol-1-yl)benzoyl]piperidine hydrochloride as a white amorphous.

Workup

  1. customreturned to room temperature
  2. stirringstirred for a while
  3. customThe organic layer was separated
  4. washwater-washed
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=50/1 to 9/1)

Sources & evidence

ORD record
ord-21160ad121914aaba408fbef8ea2a045
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

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