Sodium Hydroxide → HCID 22990165, compound

HRID 1169425Notes

Reaction equation

HRID 1169425 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[O:17][CH2:16][CH2:15][C:14]([C:18]([N:20]4[CH2:25][CH2:24][CH:23]([NH:26]C(=O)C(F)(F)F)[CH2:22][CH2:21]4)=[O:19])=[CH:13][C:12]=3[CH:33]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[NH2:26][CH:23]1[CH2:24][CH2:25][N:20]([C:18]([C:14]2[CH2:15][CH2:16][O:17][C:11]3[CH:10]=[CH:9][C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=4)=[CH:33][C:12]=3[CH:13]=2)=[O:19])[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 229900891-(7-(4-Methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbonyl)-4-trifluoroacetamidopiperidine

Product 1

HCID 22990165HCID 22990165, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1-(7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbonyl)-4-trifluoroacetamidopiperidine (1.6 g) dissolved in methanol (100 ml) was added a 1 N aqueous solution of sodium hydroxide (7 ml), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated and was then 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 4-amino-1-(7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carbonyl)piperidine (compound 76) (1.1 g) as colorless prisms.

Workup

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

Sources & evidence

ORD record
ord-6e7641c33df34888844a5af7c2b9c833
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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