Methyl bromoacetate → Methyl 2-(4-benzhydrylpiperazin-1-yl)acetate

HRID 1290876Notes

Reaction equation

HRID 1290876 reaction equation
[CH3:1][O:2][C:3](=[O:6])[CH2:4]Br.[CH:7]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH:7]([N:20]1[CH2:25][CH2:24][N:23]([CH2:4][C:3]([O:2][CH3:1])=[O:6])[CH2:22][CH2:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 70048Benzhydrylpiperazine

Product 1

HCID 789874Methyl 2-(4-benzhydrylpiperazin-1-yl)acetateYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylbromoacetate (2,75 g, 18 mmol) was added dropwise to a solution of benzhydrylpiperazin (4.5 g, 18 mmol) in THF (150 ml). The reaction was stirred for 30 minutes at room temperature and a white precipitate formed. THF was removed under reduced pressure and the residue partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with saturated sodium bicarbonate solution and water before drying over magnesium sulphate, filtration and removal of solvent to leave (4-benzhydrylpiperazin-1-yl)-acetic acid, methyl ester as a pale brown oil (2.80 g, 48%).

Workup

  1. customa white precipitate formed
  2. customTHF was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. washThe organic layer was washed with saturated sodium bicarbonate solution and water
  5. dry with materialbefore drying over magnesium sulphate, filtration and removal of solvent

Sources & evidence

ORD record
ord-7d4dd56fbe0d4f84a76915548fe477ce
Source dataset
uspto-grants-1998_05
Patent number
US05753671

Reaction notes

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