Sodium Hydroxide → N-(1-(tetrahydropyran-4-yl)piperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide

HRID 1169397Notes

Reaction equation

HRID 1169397 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8]([C:10]2[CH2:11][CH2:12][O:13][C:14]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)=[CH:17][C:15]=3[CH:16]=2)=[O:9])[CH2:3][CH2:2]1.[O:28]1[CH2:33][CH2:32][C:31](=O)[CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[O:28]1[CH2:33][CH2:32][CH:31]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C:8]([C:10]3[CH2:11][CH2:12][O:13][C:14]4[CH:20]=[CH:19][C:18]([C:21]5[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=5)=[CH:17][C:15]=4[CH:16]=3)=[O:9])[CH2:5][CH2:6]2)[CH2:30][CH2:29]1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 22990182N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide

Product 1

HCID 9889788N-(1-(tetrahydropyran-4-yl)piperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamideYield 70.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (0.15 g) and tetrahydro-4H-pyran-4-one (0.06 g) dissolved in 1,2-dichloroethane (7 ml) was added under ice cooling sodium triacetoxyborohydride (0.13 g), and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was neutralized with a 1 N aqueous solution of sodium hydroxide, was then concentrated and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain crude crystals. The crude crystals were recrystallized from ethyl acetate/hexane to obtain N-(1-(tetrahydropyran-4-yl)piperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 56) (0.13 g) as colorless prisms.

Workup

  1. additionwas added under ice
  2. concentrationwas then concentrated
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialan aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate
  6. customThe resulting organic layer was evaporated under reduced pressure
  7. customto remove the solvent
  8. customto obtain crude crystals
  9. customThe crude crystals were recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-5fa4f3b0d2d642feb7b11d1ba02cab55
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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