Hydrochloric Acid → 7-(4-Biphenylyl)methoxy-3-(N,N-dimethylamino) methyl-1,2,3,4-tetrahydroquinoline hydrochloride

HRID 2269727Notes

Reaction equation

HRID 2269727 reaction equation
[CH3:1][N:2]([CH2:4][CH:5]1[CH2:14][C:13]2[C:8](=[CH:9][C:10]([OH:15])=[CH:11][CH:12]=2)[NH:7][CH2:6]1)[CH3:3].[C:16]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[ClH:49]>C1COCC1>[ClH:49].[C:16]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:17]=[CH:18][C:19]([CH2:22][O:15][C:10]2[CH:9]=[C:8]3[C:13]([CH2:14][CH:5]([CH2:4][N:2]([CH3:1])[CH3:3])[CH2:6][NH:7]3)=[CH:12][CH:11]=2)=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 19186(1,1'-Biphenyl)-4-methanolHCID 219397443-(Dimethylamino)methyl-1,2,3,4-tetrahydro-7-quinolinol

Product 1

HCID 183615217-(4-Biphenylyl)methoxy-3-(N,N-dimethylamino) methyl-1,2,3,4-tetrahydroquinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethylazodicarboxylic acid (348 mg) was added dropwise to a THF solution (20 ml) of 3-(dimethylamino)methyl-1,2,3,4-tetrahydro-7-quinolinol (344 mg), 4-biphenylylmethanol (368 mg), and triphenylphosphine (525 mg). The reaction mixture was stirred at room temperature for one hour, which was poured into 1N hydrochloric acid and washed with ethyl acetate. The aqueous layer was neutralized with 1N aqueous sodium hydroxide solution, to which was added a saturated aqueous sodium bicarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/4), converted into its hydrochloride, and then recrystallized from ethanol-IPE to give the entitled compound (214 mg).

Workup

  1. washwashed with ethyl acetate
  2. additionwas added a saturated aqueous sodium bicarbonate solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/4)
  8. customrecrystallized from ethanol-IPE

Sources & evidence

ORD record
ord-d87cbf4b28aa499d9db3a51e31c77915
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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