Dimethyl Sulfide → N-benzyl-2-(2-bromophenyl)ethanamine

HRID 1057478Notes

Reaction equation

HRID 1057478 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O.CSC>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][NH:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 1068Dimethyl SulfideHCID 10892034N-benzyl-2-(2-bromophenyl)acetamide

Product 1

HCID 11055371N-benzyl-2-(2-bromophenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Bromophenyl)-N-(phenylmethyl)acetamide was dissolved THF (0.2 M), followed by addition of BH3.DMS (3 eq), and the reaction was heated to reflux with stirring. After 2 hrs, the mixture was cooled to room temerature, and quenched with excess 10% HCl. The mixture was heated to reflux for 1 hr, and then cooled to room temperature. After washing with EtOAc, the aqueous phase was made alkaline with 10% sodium carbonate, and extracted with EtOAc. The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was triturated with EtOAc to afford a colorless solid. EI-MS m/z 290/292 (M+H)+

Workup

  1. additionfollowed by addition of BH3
  2. temperatureto reflux
  3. temperaturethe mixture was cooled to room temerature
  4. customquenched with excess 10% HCl
  5. temperatureThe mixture was heated
  6. temperatureto reflux for 1 hr
  7. washAfter washing with EtOAc
  8. extractionextracted with EtOAc
  9. washThe organic phase was washed with brine
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe residue was triturated with EtOAc
  14. customto afford a colorless solid

Sources & evidence

ORD record
ord-763dc93c3042457ebeb88c9c6847b979
Source dataset
uspto-grants-2003_02
Patent number
US06514964B1

Reaction notes

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