Reaction #44892

Reaction equation

oxalic acid

2-(1H-Indol-3-ylsulfanyl)-N,N-dimethyl benzamide

borane

Methanol

→

[2-(1H-Indol-3-ylsulfanyl)benzyl]dimethyl amine

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture stirred at room temperature for 30 min
2. 2
   Otherevaporated in vacuo
3. 3
   workup.DISSOLUTIONThe mixture was redissolved in ethyl acetate (100 mL)
4. 4
   Washwashed with saturated sodium hydrogen carbonate (20 mL)
5. 5
   Dryingdried over anhydrous MgSO4
6. 6
   Otherevaporated in vacuo
7. 7
   OtherThe product was crystallized as an oxalate salt by dissolution in acetone

Procedure

2-(1H-Indol-3-ylsulfanyl)-N,N-dimethyl benzamide (1 mmol) was dissolved in dry tetrahydrofuran (30 mL). To the mixture was added 3 mL 1 M borane in tetrahydrofuran and the mixture was stirred at room temperature for 24 hours. Methanol (5 mL) was added and the mixture stirred at room temperature for 30 min and then evaporated in vacuo. The mixture was redissolved in ethyl acetate (100 mL) and washed with saturated sodium hydrogen carbonate (20 mL), dried over anhydrous MgSO4 and evaporated in vacuo. The product was crystallized as an oxalate salt by dissolution in acetone and addition of one equivalent of oxalic acid.

Source