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

HRID 1169395Notes

Reaction equation

HRID 1169395 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[CH2:18][CH2:19][O:20][C:21]3[CH:27]=[CH:26][C:25]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)=[CH:24][C:22]=3[CH:23]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C.[OH-].[Na+]>C(OCC)(=O)C>[NH:8]1[CH2:9][CH2:10][CH:11]([NH:14][C:15]([C:17]2[CH2:18][CH2:19][O:20][C:21]3[CH:27]=[CH:26][C:25]([C:28]4[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=4)=[CH:24][C:22]=3[CH:23]=2)=[O:16])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21866389Hydrogen chloride-ethyl acetateHCID 22989985N-[1-(t-butoxycarbonyl)piperidin-4-yl]-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide

Product 1

HCID 22990182N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To N-[1-(t-butoxycarbonyl)piperidin-4-yl]-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (1.56 g) dissolved in ethyl acetate (100 ml) was added 4 N hydrochloric acid/ethyl acetate (25 ml), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was mixed with a 1 N aqueous solution of sodium hydroxide and was extracted with ethyl acetate. The organic layer was washed with water and an aqueous saturated solution of sodium chloride, and then was dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent to obtain N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 54) (1.1 g) as colorless prisms.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialan aqueous saturated solution of sodium chloride, and then was dried with anhydrous magnesium sulfate
  4. customThe resulting organic layer was evaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-7a362dff01bb4a27977655bcc9865b3e
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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