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

HRID 1166549Notes

Reaction equation

HRID 1166549 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.N(C(OCC)=O)=NC(OCC)=O.[ClH:61]>C1COCC1>[ClH:61].[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

7

Reactant 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 19186(1,1'-Biphenyl)-4-methanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 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

To a solution of 3-(dimethylamino)methyl-1,2,3,4-tetrahydro-7-quinolinol (344 mg), 4-biphenylylmethanol (368 mg), and triphenylphosphine (525 mg) in THF (20 ml) was added diethyl azodicarboxylate (348 mg). After stirring at room temperature for one hr, the reaction mixture was poured into 1 N aqueous hydrochloric acid and washed with ethyl acetate. The water layer was neutralized by 1 N aqueous sodium hydroxide, diluted with saturated aqueous sodium bicarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate: hexane=1:4) and converted into its hydrochloride, which was further recrystallized from ethanol-diisopropyl ether to obtain the titled compound (214 mg).

Workup

  1. washwashed with ethyl acetate
  2. additiondiluted with saturated aqueous sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate: hexane=1:4)
  8. customwas further recrystallized from ethanol-diisopropyl ether

Sources & evidence

ORD record
ord-73a87b0548e1421797c4606ce33b4b40
Source dataset
uspto-grants-2003_09
Patent number
US06613805B2

Reaction notes

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