Dimethylamine → HCID 58591561, compound

HRID 746601Notes

Reaction equation

HRID 746601 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=2

Participants

3

Reactant 2

HCID 674DimethylamineHCID 58591583HCID 58591583, compound

Product 1

HCID 58591561HCID 58591561, compoundYield 94%

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.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with sat. NaHCO3 (2×)
  4. extractionsubsequently extracted with 1N HCl (3×)
  5. extractionextracted with EtOAc (4×)
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d11cca4c0984408a5af82a46324993e
Source dataset
uspto-grants-2008_07
Patent number
US07393865B2

Reaction notes

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