Hydrochloric Acid → HCID 18333131, compound

HRID 2269754Notes

Reaction equation

HRID 2269754 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([N:14]([CH2:16][CH:17]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([C:27](=O)[CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:32][CH:31]=2)[CH2:18]1)[CH3:15])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.Cl.[OH-].[Na+]>C1COCC1>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[CH2:7]([N:14]([CH2:16][CH:17]1[CH2:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]([CH2:27][CH2:28][CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:34][CH:35]=2)[CH2:18]1)[CH3:15])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 18333085HCID 18333085, compound

Product 1

HCID 18333131HCID 18333131, compoundYield 401.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-(N-Benzyl-N-methylamino)methyl-1-[3-(4-biphenylyl]propanoyl)-1,2,3,4-tetrahydroquinoline oxalate (0.800 g) was converted into a free form, which was dissolved in THF (5 ml). 1M Borane-THF complex (3 ml) was added to the reaction mixture, which was heated under reflux for 30 minutes, then left standing for cooling. Water (0.5 ml) and 6N hydrochloric acid (2 ml) were added to the reaction mixture, which was stirred at room temperature for 12 hours. The reaction mixture was made basic by adding 1N aqueous sodium hydroxide solution and 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=1/50). A methanol solution (3 ml) of oxalic acid dehydrate (149 mg) was added to a methanol solution (10 ml) of the residue, which was concentrated. Ethyl acetate was added to the residue, and the precipitates were collected by filtration to give the entitled compound (3.130 g) as an amorphous powder.

Workup

  1. addition1M Borane-THF complex (3 ml) was added to the reaction mixture, which
  2. temperaturewas heated
  3. temperatureunder reflux for 30 minutes
  4. waitleft
  5. temperaturefor cooling
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate/hexane=1/50)
  11. additionA methanol solution (3 ml) of oxalic acid dehydrate (149 mg) was added to a methanol solution (10 ml) of the residue, which
  12. concentrationwas concentrated
  13. additionEthyl acetate was added to the residue
  14. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-5fefe0a454cf4e1fae2203c5d7ddc067
Source dataset
uspto-grants-2001_12
Patent number
US06329389B1

Reaction notes

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