Triethylamine → HCID 21108198, compound

HRID 1766017Notes

Reaction equation

HRID 1766017 reaction equation
[C:1]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:2](C(Cl)=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.Cl.Cl.[CH3:18][N:19]([CH3:33])[CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[C:25]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH2:28][CH2:27][CH2:26]2.C(N(CC)CC)C.[C:41](OCC)(=[O:43])C>CN(C)C=O>[C:10]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=[CH:12][C:13]([C:41]([N:29]2[C:30]3[C:25](=[CH:24][C:23]([CH2:22][CH2:21][CH2:20][N:19]([CH3:18])[CH3:33])=[CH:32][CH:31]=3)[CH2:26][CH2:27][CH2:28]2)=[O:43])=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 12563768[1,1'-Biphenyl]-2-carbonyl chlorideHCID 17848759HCID 17848759, compound

Product 1

HCID 21108198HCID 21108198, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Biphenylcarbonyl chloride (327 mg, 1.51 mmol) was added to a solution of N,N-dimethyl-3-(1,2,3,4-tetrahydro-6-quinolinyl)-1-propanamine dihydrochloride (400 mg, 1.37 mmol) obtained in Reference Example 4 and triethylamine (669 ml, 4.81 mmol) in dimethylformamide under cooling with ice-bath, and the mixture was stirred at room temperature for 3 days. Ethyl acetate was added to the reaction solution which was then washed with an aqueous saturated sodium bicarbonate solution and a saturated saline solution and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=3:1) and crystallized from hexane, whereby the title compound (113 mg) was obtained as colorless powder with a mp. of 100 to 101° C.

Workup

  1. temperatureunder cooling with ice-bath
  2. washwas then washed with an aqueous saturated sodium bicarbonate solution
  3. dry with materiala saturated saline solution and dried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resultant residues were purified by alumina column chromatography (developing solvent; hexane:ethyl acetate=3:1)
  6. customcrystallized from hexane, whereby the title compound (113 mg)
  7. customwas obtained as colorless powder with a mp. of 100 to 101° C.

Sources & evidence

ORD record
ord-0c51551612fd4b8a91e4c8d8c8674120
Source dataset
uspto-grants-2007_06
Patent number
US07229986B2

Reaction notes

Loading…