Dimethyl Sulfide → (R)-1-Benzyl-3-(4-bromobenzyl)piperazine

HRID 1159106Notes

Reaction equation

HRID 1159106 reaction equation
[CH2:1]([N:8]1[CH2:13][C:12](=O)[NH:11][C@H:10]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][CH:17]=2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(C)C>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([Br:22])=[CH:20][CH:21]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 1068Dimethyl Sulfide2×HCID 57743624HCID 57743624, compound

Product 1

HCID 57743499(R)-1-Benzyl-3-(4-bromobenzyl)piperazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (R)-1-benzyl-3-(4-bromo-benzyl)-piperazine-2,5-dione (0.5 g, 1.34 mmol) in THF (10 mL) was added 2M B3.SMe2 (2.68 mL, 5.36 mmol). The mixture was stirred in RT under argon for 4 days; more 2M B3.SMe2 (2.68 mL, 5.36 mmol) was added and stirred for 3 days. Reaction mixture was quenched with EtOH (3 mL) and removed the solvent in rotavap, added EtOH (5 mL) and stirred at 70° C. for 2 hr and concentrated to give colorless oil as a crude product. MS (ESI) 345 (M+H).

Workup

  1. stirringstirred for 3 days
  2. customReaction mixture
  3. customwas quenched with EtOH (3 mL)
  4. customremoved the solvent in rotavap
  5. additionadded EtOH (5 mL)
  6. stirringstirred at 70° C. for 2 hr
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7821e4b5bd244730b72e16750c37c6f7
Source dataset
uspto-grants-2010_10
Patent number
US07812024B2

Reaction notes

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