Dimethylformamide → 2-[N-Benzyl-N-(3,3-diphenylpropyl)amino]methyl-6-methoxytetralin

HRID 382950Notes

Reaction equation

HRID 382950 reaction equation
Cl.[CH2:2]([NH:9][CH2:10][CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=2)[CH2:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:23]1([CH:29]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:30][CH2:31]I)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:2]([N:9]([CH2:10][CH:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:21][CH3:22])[CH:17]=2)[CH2:12]1)[CH2:31][CH2:30][CH:29]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 155128783,3-Diphenylpropyl iodideHCID 229986252-(N-benzylamino)methyl-6-methoxytetralin hydrochloride

Product 1

HCID 183615812-[N-Benzyl-N-(3,3-diphenylpropyl)amino]methyl-6-methoxytetralinYield 37.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-(N-benzylamino)methyl-6-methoxytetralin hydrochloride (0.602 g; obtained in Reference Example 6), 3,3-diphenylpropyl iodide (0.803 g) and potassium carbonate (0.800 g) were added to DMF (20 ml). The reaction mixture was stirred at room temperature for 24 hours, and water was added thereto, which was then extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated. The residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1) to obtain the entitled compound (0.335 g).

Workup

  1. extractionwhich was then extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-742c9a88866d4323b2ef711663575cc9
Source dataset
uspto-grants-2001_10
Patent number
US06310107B1

Reaction notes

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