2-Cyclohexylacetaldehyde → HCID 22990192, compound

HRID 1169401Notes

Reaction equation

HRID 1169401 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.[CH:28]1([CH2:34][CH:35]=O)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH:28]1([CH2:34][CH2:35][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)[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

5

Reactant 3

HCID 3166272-CyclohexylacetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 22990182N-(4-piperidinyl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide

Product 1

HCID 22990192HCID 22990192, compoundYield 81.8%

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 cyclohexylactaldehyde (0.07 g) dissolved in 1,2-dichloroethane (10 ml) was added under ice cooling sodium triacetoxyborohydride (0.12 g), and the resulting mixture was stirred at room temperature overnight under a nitrogen atmosphere. The reaction mixture was evaporated to remove the solvent, 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 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-(2-cyclohexylethyl)piperidin-4-yl)-7-(4-methylphenyl)-2,3-dihydro-1-benzooxepine-4-carboxamide (compound 60) (0.16 g) as colorless prisms.

Workup

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

Sources & evidence

ORD record
ord-0e2aeb959531457c8fd3196a72825441
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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