Potassium Carbonate → n-[2-(n,n-Dimethylamino)methyl-6-tetralinyl]-(4'-methoxybiphenyl-4-yl)carboxamide

HRID 1242930Notes

Reaction equation

HRID 1242930 reaction equation
C1C=CC2N(O)N=NC=2C=1.[NH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[CH2:18][CH:17]([CH2:22][N:23]([CH3:25])[CH3:24])[CH2:16][CH2:15]2.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:42]=[CH:41][C:37]([C:38](O)=[O:39])=[CH:36][CH:35]=2)=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C1C=CN=CC=1)C.CN(C=O)C.C(N(CC)CC)C>[CH3:24][N:23]([CH2:22][CH:17]1[CH2:16][CH2:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([NH:11][C:38]([C:37]3[CH:36]=[CH:35][C:34]([C:31]4[CH:32]=[CH:33][C:28]([O:27][CH3:26])=[CH:29][CH:30]=4)=[CH:42][CH:41]=3)=[O:39])[CH:13]=2)[CH2:18]1)[CH3:25]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 757711-HydroxybenzotriazoleHCID 27595524'-Methoxy(1,1'-biphenyl)-4-carboxylic acidHCID 219397216-[(Dimethylamino)methyl]-5,6,7,8-tetrahydronaphthalen-2-amine

Product 1

HCID 9844702n-[2-(n,n-Dimethylamino)methyl-6-tetralinyl]-(4'-methoxybiphenyl-4-yl)carboxamideYield 57.9%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent3×HCID 8471TriethylamineSolvent

Procedure

DMF solution (0.25 ml) of 2M HOBt, DMF solution (0.30 ml) of 2M WSCD, triethylamine (0.14 ml) and DMAP (0.132 g) were added to DMF solution (3 ml) of 6-amino-2-(N,N-dimethylamino)methyltetralin (0.139 g) and 4-(4-methoxy phenyl) benzoic acid (0.118 g). After the reaction mixture was stirred at room temperature for 12 hours, 10% potassium carbonate solution was added, 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 resulting crude crystal was washed with diethyl ether, which was recrystallized using ethyl acetate-hexane, to give the titled compound (0.124 g).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  3. customdried
  4. concentrationconcentrated
  5. washThe resulting crude crystal was washed with diethyl ether, which
  6. customwas recrystallized

Sources & evidence

ORD record
ord-cb3a2a582ed54c7ea90cb34b1c527f82
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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