Water → HCID 18472249, compound

HRID 565953Notes

Reaction equation

HRID 565953 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[CH2:20][CH2:21][O:22][C:23]3[CH:29]=[CH:28][C:27]([C:30]4[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=4)=[CH:26][C:24]=3[CH:25]=2)=[O:18])=[CH:12][CH:11]=1)=[O:9].B.[Na].O>CO>[OH:9][CH:8]([CH:3]1[CH2:4][CH2:5][CH2:6][CH2:7][N:2]1[CH3:1])[C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]([C:19]2[CH2:20][CH2:21][O:22][C:23]3[CH:29]=[CH:28][C:27]([C:30]4[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=4)=[CH:26][C:24]=3[CH:25]=2)=[O:18])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 18472360HCID 18472360, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 18472249HCID 18472249, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (40ml) was dissolved N-(4-(1-methyl-piperidin-2-ylcarbonyl)-phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (0.1g) under ice-cooling, and to the mixture was added sodium boron hydride (10mg). The mixture was stirred for 15 minutes, and to the mixture was added water. The mixture was concentrated and extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/methanol/triethylamine) to give crude crystals, which were recrystallized from ethanol-ethyl acetate-hexane to give N-(4-(hydroxy(1-methylpiperidin-2-yl)methyl)-phenyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzoxepine-4-carboxamide (Compound 158) (0.07g) as colorless crystals.

Workup

  1. temperaturecooling
  2. concentrationThe mixture was concentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried with anhydrous magnesium sulfate
  6. customUnder reduced pressure, the solvent was evaporated
  7. customthe residue was purified with silica gel column (ethyl acetate/methanol/triethylamine)
  8. customto give crude crystals, which
  9. customwere recrystallized from ethanol-ethyl acetate-hexane

Sources & evidence

ORD record
ord-d431521f70f04bf89e8ec937c783bc66
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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