Propargyl bromide → tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylate

HRID 1985622Notes

Reaction equation

HRID 1985622 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([O-])([O-])=O.[Na+].[Na+].Br[CH2:21][C:22]#[CH:23]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:23][C:22]#[CH:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 11287538tert-Butyl 4-(prop-2-yn-1-yl)piperazine-1-carboxylateYield 58.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To the degassed solution of piperazine-1-carboxylic acid tert-butyl ester (1.0 g, 5.37 mmol) in acetonitrile (10 ml) were added Na2CO3 (1.708 g, 16.11 mmol) and mixture was stirred for 20 min. The suspension was heated to 50° C. and 3-bromo-propyne (0.9 mL, 8.055 mmol) was added. The solvent was evaporated and the residue was extracted with Et-Ac and water (2×50 mL). Organic layer was washed with NaCl and NaHCO3 (2×50 ml). The organic layer was dried over K2CO3 and evaporated in vacuum yielding (0.70 g) oil title intermediate.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue was extracted with Et-Ac and water (2×50 mL)
  3. washOrganic layer was washed with NaCl and NaHCO3 (2×50 ml)
  4. dry with materialThe organic layer was dried over K2CO3
  5. customevaporated in vacuum

Sources & evidence

ORD record
ord-8f0d69a873464196bcc8cc58246934b5
Source dataset
uspto-grants-2009_06
Patent number
US07547679B2

Reaction notes

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