Ethyl Acetate → Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylate

HRID 549081Notes

Reaction equation

HRID 549081 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(=O)(O)[O-].[Na+].C(OCC)(=O)C>C(#N)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([N:20]2[CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:22][CH2:21]2)=[CH:3][CH:4]=1)#[N:7]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 145174-FluorobenzonitrileHCID 143452tert-Butyl piperazine-1-carboxylateHCID 516892Sodium Bicarbonate

Product 1

HCID 2795512Tert-butyl 4-(4-cyanophenyl)piperazine-1-carboxylateYield 23.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-fluorobenzonitrile (3.6 g) and N-tert-butyloxycarbonylpiperazine (5.58 g) in acetonitrile (60 mL) was heated at 80° C. for 72 hours. The reaction mixture was then cooled to room temperature and then treated with a mixture of sodium bicarbonate solution and ethyl acetate (300 mL, 1:1, v/v). The organic phase was separated and then evaporated. The residue was subjected to chromatography on silica gel eluting with a mixtures of heptane and ethyl acetate (from 3:7 to 1:1, v/v) to give the title compound (2 g) as a white solid.

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customThe organic phase was separated
  3. customevaporated

Sources & evidence

ORD record
ord-8c6b6da305574722a7049480b0237f16
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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