Hydrochloric Acid → 8-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthalene

HRID 2371938Notes

Reaction equation

HRID 2371938 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([N:12]([CH2:16][CH2:17][CH3:18])[CH2:13][CH2:14][CH3:15])[CH2:8][CH2:7]2.C([BH3-])#N.[Na+].Cl.[OH-].[Na+]>O1CCCC1>[CH2:16]([N:12]([CH2:13][CH2:14][CH3:15])[CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([Br:1])[CH:3]=[CH:4][CH:5]=2)[CH2:10]1)[CH2:17][CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 190432078-Bromo2-dipropylamino-3,4-dihydronaphthalene

Product 1

HCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Alternatively, to the 8-bromo-2-dipropylamino-3,4-dihydronaphthalene (44.4 mMol) in tetrahydrofuran (100 ml) was added sodium cyano-borohydride (2.86 gm, 45.5 mMol) and the suspension was saturated with hydrogen chloride. After stirring for four hours the reaction mixture was poured into 15% aqueous sodium hydroxide (500 ml) and was stirred an additional two hours. This mixture was extracted with diethyl ether, and the ether extracts were combined, washed with water, washed with saturated aqueous sodium chloride, dried (Na2SO4) and concentrated in vacuo to give the crude title compound as a light orange oil. Purification by basic alumina chromatography (dichloromethane) gave the product as a light yellow oil (7.8 gm, 57%).

Workup

  1. stirringwas stirred an additional two hours
  2. extractionThis mixture was extracted with diethyl ether
  3. washwashed with water
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customto give the crude title compound as a light orange oil
  8. customPurification by basic alumina chromatography (dichloromethane)

Sources & evidence

ORD record
ord-dc2485b98d7741d9961eea885bf0530d
Source dataset
uspto-grants-1992_03
Patent number
US05096908

Reaction notes

Loading…