Acetic Acid → (S)-2-Benzyl-4-(4-bromo-benzyl)-1-methyl-piperazine

HRID 737148Notes

Reaction equation

HRID 737148 reaction equation
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.[C:24](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1.C(=O)(O)[O-].[Na+]>[CH2:1]([C@H:8]1[CH2:9][N:10]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([Br:21])=[CH:19][CH:20]=2)[CH2:11][CH2:12][N:13]1[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 578494623-(S)-benzyl-1-(4-bromobenzyl)-piperazine

Product 1

HCID 57849477(S)-2-Benzyl-4-(4-bromo-benzyl)-1-methyl-piperazineYield 82%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 369 mg of 3-(S)-benzyl-1-(4-bromobenzyl)-piperazine in 3 mL of tetrahydrofuran was added 0.8 mL of formaldehyde and 0.15 mL acetic acid. After 2 h, 453 mg of sodium triacetoxyborohydride was added and the reaction was stirred overnight. Diluted carefully with aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The combined organics were washed with brine, dried with sodium sulfate, filtered and concentrated in vacuo. Used crude in subsequent reactions. 82% yield. ES MS (+)m/z 361

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organics were washed with brine
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fd0787d7fff346f0a83885ddd409c5f9
Source dataset
uspto-grants-2009_09
Patent number
US07595397B2

Reaction notes

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