Triethylamine → Tert-butyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate

HRID 1039122Notes

Reaction equation

HRID 1039122 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 46785870Tert-butyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylateYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1-(tert-butoxycarbonyl)piperazine (1.38 g, 7.41 mmol) in acetonitrile (10 mL) was stirred with triethylamine (2.07 mL, 14.8 mmol) and methyl 2-bromoacetate (1.02 mL, 11.1 mmol) at room temperature for 4 hours and then filtered. The filtrate was concentrated, and after addition of saturated aqueous ammonium chloride, extracted with ethyl acetate. The organic phase was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the desired product (yield 83%).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. additionafter addition of saturated aqueous ammonium chloride
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with saturated aqueous ammonium chloride and saturated aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a0f7f41e49f34c3d96e32119a9814998
Source dataset
uspto-grants-2013_10
Patent number
US08552031B2

Reaction notes

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