Hydrochloric Acid → HCID 53917738, compound

HRID 2287831Notes

Reaction equation

HRID 2287831 reaction equation
[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[C@H:5]1[CH2:14][C:13]2[CH:12]=[C:11]([C:15]([NH2:17])=O)[CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6]1)[CH2:2][CH3:3].O.Cl.[OH-].[Na+]>O1CCCC1>[CH2:18]([N:4]([CH2:1][CH2:2][CH3:3])[C@H:5]1[CH2:14][C:13]2[CH:12]=[C:11]([CH2:15][NH2:17])[CH:10]=[CH:9][C:8]=2[CH2:7][CH2:6]1)[CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15703613HCID 15703613, compound

Product 1

HCID 53917738HCID 53917738, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the (R)-7-(dipropylamino)-5,6,7,8-tetrahydro-2-naphthalenecarboxamide (8) (8.68 g) in dry tetrahydrofuran was stirred at room temperature and borane dimethylsulfide complex (10.0 M, 11.1 ml) was slowly added. When the initial reaction subsided, the mixture was heated at reflux for 2 days. The mixture was cooled in ice, and water was added dropwise. When the evolution of gas ceased, 10% hydrochloric acid (75 ml) was added, and the mixture was refluxed for 2 hours. The mixture was cooled in ice and basified with solid sodium hydroxide. The mixture was extracted with diethylether and then with 2:1 diethylether/tetrahydrofuran. The combined extracts were washed with brine and dried (MgSO4). The solvent was removed under vacuum to leave the title compound a yellow oil (8.15 g) which was used without further purification.

Workup

  1. additionborane dimethylsulfide complex (10.0 M, 11.1 ml) was slowly added
  2. customWhen the initial reaction
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 2 days
  5. temperatureThe mixture was cooled in ice
  6. temperaturethe mixture was refluxed for 2 hours
  7. extractionThe mixture was extracted with diethylether
  8. washThe combined extracts were washed with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-2ba75c18427a4a158fde1f8898f2721b
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

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