Phenylacetyl chloride → 6-[4-(Benzylcarbonylamino)benzyloxy]-2-[(N,N-dimethylamino)methyl]tetralin

HRID 1242881Notes

Reaction equation

HRID 1242881 reaction equation
C1COCC1.[C:6]1([CH2:12][C:13](Cl)=[O:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH2:29][CH:28]([CH2:33][N:34]([CH3:36])[CH3:35])[CH2:27][CH2:26]3)=[CH:19][CH:18]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.N1C=CC=CC=1>[CH2:12]([C:13]([NH:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH2:29][CH:28]([CH2:33][N:34]([CH3:35])[CH3:36])[CH2:27][CH2:26]3)=[CH:19][CH:18]=1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 219397226-(4-Aminobenzyloxy)-2-[(N,N-dimethylamino)methyl]tetralin

Product 1

HCID 219400516-[4-(Benzylcarbonylamino)benzyloxy]-2-[(N,N-dimethylamino)methyl]tetralinYield 42.3%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

THF solution (1 ml) of phenylacetyl chloride (200 mg) was added dropwise to pyridine solution (6 ml) of 6-[(4-aminobenzyl)oxy]-2-[(N,N-dimethylamino)methyl]tetralin (300 mg) under ice-cooling, which was stirred for 15 minutes. After stirring at room temperature for further 15 minutes, saturated sodium bicarbonate solution was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using alumina column chromatography (development solvent; hexane˜hexane:ethyl acetate=2:1), and recrystallized to give the titled compound (175 mg).

Workup

  1. temperaturecooling
  2. stirringAfter stirring at room temperature for further 15 minutes
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customrecrystallized

Sources & evidence

ORD record
ord-98a33b5091a549569949afc7ea2391ef
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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