Sodium Bicarbonate → HCID 67238887, compound

HRID 1912030Notes

Reaction equation

HRID 1912030 reaction equation
[C:1]([O-:4])(O)=O.[Na+].[S:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[CH2:11][CH2:12]O.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1S([O-])(=O)=O)([O-])=O>C(#N)C>[CH2:18]([CH:11]([C:7]1[S:6][CH:10]=[CH:9][CH:8]=1)[CH2:12][NH:14][C@H:17]1[CH2:22][CH2:21][C:20]2[C:1]([OH:4])=[CH:11][CH:7]=[CH:8][C:19]=2[CH2:18]1)[CH2:17][CH3:22]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 87320561HCID 87320561, compound

Product 1

HCID 67238887HCID 67238887, compoundYield 130.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10 g of (S)-(−)-2-(N-propylamino)-5-hydroxytetraline, S-(III), obtained according to Example 2 were mixed with 9 g of NaHCO3 (2.2 equivalents) and 16 g of 2-(2-thienyl)ethanol 2-nitrobenzenesulfonate (1.05 equivalents) in 80 mL of acetonitrile. The mixture was refluxed for 9 hours, and then cooled and filtered for removal of suspended salts. 60 mL of water were added to the filtrate and concentrated by distillation for removal of acetonitrile. 40 mL of toluene were added and the layers were separated. The organic layer was twice washed with 10% NaHCO3. Then, 50 mL of water and H3PO4 were added to pH=1-2. After layer separation, the aqueous acid layer was neutralized with 30% K2CO3 to pH=7-7.5 and extracted with 20 mL of ethyl acetate. The organic layer was washed with 10 mL of water, concentrated by distillation from the solvent to provide 10 g of (6S)-(−)-5,6,7,8-tetrahydro-6-[propyl-(2-thienyl)ethyl]amino-1-naphthol, S-(I), as a white solid (70% yield).

Workup

  1. temperatureThe mixture was refluxed for 9 hours
  2. temperaturecooled
  3. filtrationfiltered for removal of suspended salts
  4. addition60 mL of water were added to the filtrate
  5. concentrationconcentrated by distillation for removal of acetonitrile
  6. addition40 mL of toluene were added
  7. customthe layers were separated
  8. washThe organic layer was twice washed with 10% NaHCO3
  9. additionThen, 50 mL of water and H3PO4 were added to pH=1-2
  10. customAfter layer separation
  11. extractionextracted with 20 mL of ethyl acetate
  12. washThe organic layer was washed with 10 mL of water
  13. concentrationconcentrated by distillation from the solvent

Sources & evidence

ORD record
ord-a303f54a9d2f49c69e9cff71687d12c6
Source dataset
uspto-grants-2013_12
Patent number
US08604242B2

Reaction notes

Loading…