Boron trifluoride etherate → 2-(3,4-Dimethoxy-phenylsulfanyl)-ethylamine

HRID 458797Notes

Reaction equation

HRID 458797 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[BH4-].[Na+].B(F)(F)F.CCOCC.C(Cl)Cl.CO>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:11][CH2:12][CH2:13][NH2:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 12698215(3,4-Dimethoxy-phenylsulfanyl)-acetonitrileHCID 21226129Dichloromethane methanol

Product 1

HCID 137594312-(3,4-Dimethoxy-phenylsulfanyl)-ethylamineYield 46.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a cold (0° C.) solution of (3,4-dimethoxy-phenylsulfanyl)-acetonitrile (7.53 g, 36.0 mmol) in anhydrous THF (41 ml), was added portionwise NaBH4 (1.22 g, 32.0 mmol) and dropwise a solution of BF3.OEt2 (5.37 ml, 20.0 mmol) in anhydrous THF (13.4 ml) over 30 min. The resulting mixture was stirred at RT for 3 h under nitrogen. The mixture was concentrated in vacuo, the residue was dissolved in CH2Cl2 and washed with HCl 37%. The aqueous phase was neutralized with NaOH 30% and extracted with CH2Cl2. The combined organic phases were dried over anhydrous MgSO4, filtered and concentrated to give a crude oil. Flash chromatography (CH2Cl2/MeOH: 9/1) gave the title product (3.6 g, 46%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in CH2Cl2
  3. washwashed with HCl 37%
  4. extractionextracted with CH2Cl2
  5. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a crude oil

Sources & evidence

ORD record
ord-b04267cb0a604f21b329902654655dfa
Source dataset
uspto-grants-2007_03
Patent number
US07192950B2

Reaction notes

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