Acetic Acid → tert-Butyl 2-(4-chlorophenyl)piperazine-1-carboxylate

HRID 1784658Notes

Reaction equation

HRID 1784658 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][C:10](=O)[CH:9]1[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.[BH4-].[Na+]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH:9]1[C:15]1[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 67117397HCID 67117397, compound

Product 1

HCID 44558599tert-Butyl 2-(4-chlorophenyl)piperazine-1-carboxylateYield 69.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Solution of 4-(tert-butoxycarbonyl)-3-(4-chlorophenyl)-piperazin-2-one (500 mg, 1.6 mmol) and acetic acid (929 μl, 16 mmol) were added to a refluxed solution of sodium borohydride (608 mg, 16 mmol) in 1,4-dioxane (5 ml) and reflux was continued. The reaction was quenched by water and extracted with dichloromethane and washed with brine and dried. After removal of the solvent, residue was purified by silica gel column chromatography to give 4-(tert-butoxycarbonyl)-3-(4-chlorophenyl)piperazine (330 mg, 69%).

Workup

  1. temperaturereflux
  2. customThe reaction was quenched by water
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. customdried
  6. customAfter removal of the solvent, residue
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f3289adec1bb49b0b7ded17da9899ca1
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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