Potassium Carbonate → 1-Boc-4-(4-Nitrobenzyl)piperazine

HRID 1882865Notes

Reaction equation

HRID 1882865 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21]Br)=[CH:19][CH:18]=1)([O-:16])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)=[CH:19][CH:18]=1)([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 235069461-Boc-4-(4-Nitrobenzyl)piperazineYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 1-piperazinecarboxylate, 1 (0.74 g, 4 mmol), and 4-nitrobenzyl bromide, 2 (0.86 g, 4 mmol), in N,N-dimethylformamide (DMF, 5 mL) was added potassium carbonate (3 g), and the reaction mixture was stirred at room temperature for 4 h. The product was extracted with ethyl acetate (50 mL), and the organic phase was washed with water (20 mL×3). The solution was dried with sodium sulfate, and solvent was removed in vacuo. The product was purified by column chromatography, eluting with ethyl acetate to afford 3 as a solid (1.22 g, 95% yield), mp 99-100° C. 1H NMR (DMSO-d6): 8.21-8.19 (d, 2H, J=8.8 Hz, Ar-H), 7.61-7.59 (d, 2H, J=8.0 Hz, Ar-H), 3.63 (s, 2H, CH2), 3.34-3.30 (m, 4H, partially obscured, 2×CH2), 2.35-2.3 (m, 4H, 2×CH2), 1.39 (s, 9H, 3×CH3). Anal. (C16H23N3O4) C, H, N.

Workup

  1. extractionThe product was extracted with ethyl acetate (50 mL)
  2. washthe organic phase was washed with water (20 mL×3)
  3. dry with materialThe solution was dried with sodium sulfate, and solvent
  4. customwas removed in vacuo
  5. customThe product was purified by column chromatography
  6. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-84cb073cb36e4dc1990d1564b30355b3
Source dataset
uspto-grants-2004_07
Patent number
US06759416B2

Reaction notes

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