Triethylamine → 2,2-Dimethyl-1-[4-(4-nitro-phenyl)-piperazin-1-yl]-propan-1-one

HRID 37844

Reaction equation

HRID 37844 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16](Cl)(=[O:21])[C:17]([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C>C(Cl)Cl>[CH3:18][C:17]([CH3:20])([CH3:19])[C:16]([N:13]1[CH2:14][CH2:15][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11][CH2:12]1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 36160592,2-Dimethyl-1-[4-(4-nitro-phenyl)-piperazin-1-yl]-propan-1-oneYield 85.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled solution of 1-(4-nitro-phenyl)-piperazine (prepared as described in Reference Example 29; 5 g, 24 mmol) in DCM (40 mL) was added pivaloyl chloride (4.36 g, 36.2 mmol) and triethylamine (8.73 mL, 60 mmol) at 0-5° C. The mixture was warmed to room temperature and stirred for 1 hour then diluted with DCM (150 mL), washed with water (2×50 mL) and brine (50 mL), dried over sodium sulfate and concentrated to dryness to afford 2,2-dimethyl-1-[4-(4-nitro-phenyl)-piperazin-1-yl]-propan-1-one (6 g, 85.7%) as a yellow solid.

Workup

  1. washwashed with water (2×50 mL) and brine (50 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-421a7e4496ac4882b82467f6fbc5e8f4
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Linked notes

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