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

HRID 1169398Notes

Reaction equation

HRID 1169398 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.[C:28]1([CH:36]=O)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>ClCCCl>[C:28]1([CH2:36][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)[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH:29]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 22990182N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamideHCID 53866598Cyclooct-1-ene-1-carbaldehyde

Product 1

HCID 70025289N-(1-(cycloocten-1-yl)methylpiperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamideYield 54.8%

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 cyclooctene-1-carbaldehyde (0.08 g) dissolved in 1,2-dichloroethane (10 ml) was added sodium triacetoxyborohydride (0.12 g) under ice cooling, 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. The residue was subjected to purification using a silica gel column (ethyl acetate) to obtain crude crystals. The crude crystals were recrystallized from ethyl acetate/diethyl ether/hexane to obtain N-(1-(cycloocten-1-yl)methylpiperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 57) (0.11 g) as colorless prisms.

Workup

  1. concentrationwas then concentrated
  2. extractionwas 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. customThe residue was subjected to purification
  8. customto obtain crude crystals
  9. customThe crude crystals were recrystallized from ethyl acetate/diethyl ether/hexane

Sources & evidence

ORD record
ord-008abae460f64fd0af626c70196d4a36
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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