tert-Butyl piperazine-1-carboxylate → HCID 68680769, compound

HRID 646891Notes

Reaction equation

HRID 646891 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([N:8]2[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]2[CH3:14])[CH:7]=1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19]>CN(C=O)C.CCOC(C)=O>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][N:28]([C:2]2[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([N:8]3[C:12]([CH3:13])=[CH:11][CH:10]=[C:9]3[CH3:14])[CH:7]=2)[CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 686806361-(5-Chloro-2-nitro-phenyl)-2,5-dimethyl-1H-pyrrole

Product 1

HCID 68680769HCID 68680769, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 1-(5-chloro-2-nitro-phenyl)-2,5-dimethyl-1H-pyrrole (73 mg, 0.29 mmol, as prepared in the previous step) in DMF (2 mL) was added piperazine-1-carboxylic acid tert-butyl ester (542 mg, 2.9 mmol) and the result was heated to 90° C. for 18 h. The reaction a diluted with EtOAc (50 mL), washed with H2O (2×25 mL), dried (Na2SO4) and concentrated in vacuo. The residue was chromtographed on a SPE column (5 g, SiO2) to afford 35 mg (30%) of the title compound as a brown solid. 1H-NMR (CDCl3; 400 MHz): δ 8.13 (d, 1H, J=9.3 Hz), 6.91-6.88 (m, 1H), 6.66 (s, 1H), 5.93 (s, 2H), 3.63-3.60 (m, 4H), 3.42-3.40 (m, 4H), 1.97 (s, 6H), 1.48 (s, 9H).

Workup

  1. customThe reaction
  2. washwashed with H2O (2×25 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4277ddeb9212441fb5b0737db6fa5103
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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