Water → 1-Boc-4-(4-Nitrobenzyl)piperazine

HRID 1485225Notes

Reaction equation

HRID 1485225 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][CH:4]=1.[N:12]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:15]2[CH2:14][CH2:13][N:12]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]2)=[CH:4][CH:5]=1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium 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

1-(Bromomethyl)-4-nitrobenzene (1.08 g, 5.00 mmol) was added to a vigorously stirred mixture of tert-butyl piperazine-1-carboxylate (1.02 g, 5.50 mmol) and sodium carbonate (0.583 g, 5.50 mmol) in DMF (5 mL) at room temperature and the resulting mixture stirred for two hours. Water (25 mL) was added, and the resulting suspension was allowed to stand for five minutes then filtered. The collected solid was washed with water (25 mL) and air-dried to give the title compound (I92) (1.523 g, 95% yield); 1H NMR (400 MHz, CDCl3) δ 8.32-8.10 (m, 2H), 7.51 (d, J=8.8 Hz, 2H), 3.59 (s, 2H), 3.52-3.39 (m, 4H), 2.43-2.34 (m, 4H), 1.45 (s, 9H). LCMS Method C: rt 4.58 min, m/z 266.1 [M-tBu+2H]+, 222.1 [M-Boc+2H]+.

Workup

  1. waitto stand for five minutes
  2. filtrationthen filtered
  3. washThe collected solid was washed with water (25 mL)
  4. customair-dried

Sources & evidence

ORD record
ord-6a1ffad972544d559a47eb1170c9852e
Source dataset
uspto-grants-2016_08
Patent number
US09421205B2

Reaction notes

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