Acetic Acid → HCID 59597295, compound

HRID 218696Notes

Reaction equation

HRID 218696 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]([CH2:25][C:26]2[CH:31]=[CH:30][C:29](NC)=[CH:28][CH:27]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:34]([BH3-])#[N:35].[Na+].[C:38](O)(=O)[CH3:39].[CH2:42](O)[CH3:43]>>[CH2:42]([N:35]([CH3:34])[C:29]1[CH:30]=[CH:31][C:26]([CH2:25][N:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:5][CH:6]=2)[C:11]([CH:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([O:23][CH3:24])[CH:21]=3)[CH2:16][CH2:15][CH2:14]2)=[O:12])=[CH:27][CH:28]=1)[CH2:43][CH2:38][CH3:39]

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 702EthanolHCID 5003444Sodium cyanoborohydrideHCID 16678175HCID 16678175, compound

Product 1

HCID 59597295HCID 59597295, compound

Procedure

N-(4-Isopropylphenyl)-7-methoxy-N-[(4-methylaminophenyl)methyl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.77 g) was dissolved in ethanol (8 mL), and butyl aldehyde (250 mg) and sodium cyanoborohydride (0.22 g) were added. Acetic acid was added to this solution to pH 5-6, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate and ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography to give N-{[4-(butylmethylamino)phenyl]methyl}-N-(4-isopropylphenyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-1-carboxamide (0.51 g).

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium hydrogencarbonate and ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5ab26adc028045448bf629d2b27fbab6
Source dataset
uspto-grants-2012_06
Patent number
US08198454B2

Reaction notes

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