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Potassium Carbonate → Tert-butyl 4-(but-3-yn-1-yl)piperazine-1-carboxylate

HRID 708325
Notes
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Reaction equation

HRID 708325 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][C:23]#[CH:24]>C(#N)C.O>[CH2:24]([N:11]1[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]1)[CH2:23][C:22]#[CH:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 110734644-Bromobut-1-yne

Product 1

HCID 72213388Tert-butyl 4-(but-3-yn-1-yl)piperazine-1-carboxylateYield 86.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent
HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-Boc-piperazine (0.5 g, 2.68 mmol) in acetonitrile (2.5 mL) was added K2CO3 (0.55 g, 4.02 mmol) followed by 4-bromo-1-butyne (0.39 g, 2.95 mmol). The mixture was heated at 60° C. for 6 h, allowed to come to room temperature, diluted with water and extracted with EtOAc (2×15 mL). The combined organic layers washed with water, brine, dried over Na2SO4 and concentrated under vacuo to afford the title compound (0.55 g, 86%); LCMS: m/z=239.10 (M+1). Method 2minLowp.

Workup

  1. customto come to room temperature
  2. extractionextracted with EtOAc (2×15 mL)
  3. washThe combined organic layers washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-73850401e58f425daf9602b359bfec31
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09174978B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes