Triethylamine → tert-Butyl 4-(2-tert-butoxy-2-oxoethyl)piperazine-1-carboxylate

HRID 2190265Notes

Reaction equation

HRID 2190265 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>C1COCC1.CCOC(C)=O.O>[C:26]([O:25][C:23](=[O:24])[CH2:22][N:4]1[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]1)([CH3:29])([CH3:28])[CH3:27]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 79177tert-Butyl bromoacetateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 45789228tert-Butyl 4-(2-tert-butoxy-2-oxoethyl)piperazine-1-carboxylateYield 87%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of tert-butyl piperazine-1-carboxylate (3.0 g, 16.1 mmol) and triethylamine (4.5 mL, 32.2 mmol) in THF (80 mL) was added tert-butyl 2-bromoacetate (2.4 mL, 16.1 mmol). The mixture was stirred at room temperature for 12 hours. The reaction mixture was diluted with EtOAc (200 mL) and H2O (100 mL). The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness. The residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2) to afford the sub-title compound (4.2 g, 87%).

Workup

  1. washThe organic phase was washed with brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by column chromatography (silica, 0-5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-6679e23fd1fd4c68914ee39a6be00e4b
Source dataset
uspto-grants-2012_12
Patent number
US08324264B1

Reaction notes

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