Diisopropylethylamine → tert-Butyl 4-(3,3,3-trifluoropropyl)-1-piperazine-carboxylate

HRID 2416651Notes

Reaction equation

HRID 2416651 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)C(C)C)(C)C.Br[CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27].C(=O)([O-])O.[Na+]>CN(C)C=O>[F:27][C:26]([F:29])([F:28])[CH2:25][CH2:24][N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium BicarbonateHCID 27251143-Bromo-1,1,1-trifluoropropane

Product 1

HCID 22633053tert-Butyl 4-(3,3,3-trifluoropropyl)-1-piperazine-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(tert-butoxycarbonyl)piperazine (5.00 g) and N,N-diisopropylethylamine (4.68 ml) in N,N-dimethylformamide (13 ml) was added 1-bromo-3,3,3-trifluoropropane (5.00 ml) at 60° C. The mixture was stirred at 60° C. for 4 hours. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate solution and extracted with hexane. The organic layer was washed successively with saturated aqueous ammonium chloride solution, aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and concentrated to give the title compound (5.38 g) as a pale yellow solid.

Workup

  1. extractionextracted with hexane
  2. washThe organic layer was washed successively with saturated aqueous ammonium chloride solution, aqueous sodium hydrogencarbonate solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-facdc45277a04f8898a6d24147b75bce
Source dataset
uspto-grants-2004_11
Patent number
US06825200B1

Reaction notes

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