Dimethylamine → (2-Benzo[b]thiophen-2-yl-ethyl)-dimethylamine
Reaction equation
[S:1]1[C:5]([CH2:6][CH2:7]OS(C)(=O)=O)=[CH:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]1=2.[CH3:17][NH:18][CH3:19]>>[S:1]1[C:5]([CH2:6][CH2:7][N:18]([CH3:19])[CH3:17])=[CH:4][C:3]2[CH:13]=[CH:14][CH:15]=[CH:16][C:2]1=2Participants
3
Conditions
- Temperature
- 80 °C
Procedure
To methanesulfonic acid 2-benzo[b]thiophen-2-yl-ethyl ester (2.93 mmol) was added dimethylamine (30 mL, 2M in EtOH) and the mixture was heated in a sealed flask for 2 hrs at 80° C. Monitoring by TLC indicated complete conversion and the mixture was concentrated in vacuo. The residue was dissolved in EtOAc, washed with sat. NaHCO3 (2×) and subsequently extracted with 1N HCl (3×). The combined HCl layers were made basic with sat. NaHCO3, extracted with EtOAc (4×) and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to give Compound 1a (2-Benzo[b]thiophen-2-yl-ethyl)-dimethyl-amine (561 mg, 94%) as a tan solid; MS(MH+)=206.