tert-Butyl piperazine-1-carboxylate → 4-(4-Acetyl-benzyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 885858Notes

Reaction equation

HRID 885858 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].CS([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=1)(=O)=O.ClCC1C=CC(C(=O)C)=CC=1>CC#N>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=2)[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylate2×HCID 124348461-(4-(Chloromethyl)phenyl)ethan-1-oneHCID 670496671-[4-(Methanesulfonylmethyl)phenyl]ethanone

Product 1

HCID 582083844-(4-Acetyl-benzyl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-Boc piperazine (485 mg, 2.61 mmol) was added to a stirred solution of a mixture of 1-(4-methanesulfonylmethyl-phenyl)-ethanone, 1-(4-chloromethyl-phenyl)-ethanone (obtained in STEP A, 580 mg) and TEA (0.522 ml, 3.75 mmol) in CH3CN (5 ml). The resulting mixture was stirred at room temperature overnight and then further TEA (0.250 ml, 1.80 mmol) and N-Boc piperazine (100 mg, 0.53 mmol) were added. After 4 h the solution was partitioned between water and AcOEt, the organic phase was dried over Na2SO4 and evaporated in vacuo. The crude mixture was purified by column chromatography (eluent: petroleum ether/AcOEt 7:3 to 6:4) to give 700 mg of 4-(4-acetyl-benzyl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. customAfter 4 h the solution was partitioned between water and AcOEt
  2. dry with materialthe organic phase was dried over Na2SO4
  3. customevaporated in vacuo
  4. customThe crude mixture was purified by column chromatography (eluent: petroleum ether/AcOEt 7:3 to 6:4)

Sources & evidence

ORD record
ord-e66ba2294a2e47ddad27b49a30aacf74
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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