Water → Tert-butyl 4-(2-(4-amino-3-nitrophenoxy)ethyl)piperazine-1-carboxylate

HRID 415112Notes

Reaction equation

HRID 415112 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1.[C:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].O>C1COCC1>[NH2:9][C:8]1[CH:10]=[CH:11][C:5]([O:4][CH2:3][CH2:2][N:25]2[CH2:24][CH2:23][N:22]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:27][CH2:26]2)=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 143452tert-Butyl piperazine-1-carboxylateHCID 154854442-(4-Amino-3-nitrophenoxy)ethyl bromide

Product 1

HCID 66623212Tert-butyl 4-(2-(4-amino-3-nitrophenoxy)ethyl)piperazine-1-carboxylateYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL flask was charged with 4-(2-bromoethoxy)-2-nitroaniline (2.2 g, 8.4 mmol) in THF (20 mL) and 4-N-boc-piperazine (1.56 g, 8.4 mmol) was added and stirred at room temperature. The reaction was monitored by LCMS. After 30 minutes, the reaction mixture was treated with deionized water (100 mL) and sonicated. The resulting solid was collected by filtration and dried at reduced pressure to give 1.75 g of tert-butyl 4-(2-(4-amino-3-nitrophenoxy)ethyl)piperazine-1-carboxylate (59% yield). MS (EI): 367 (MH+).

Workup

  1. additionwas added
  2. customsonicated
  3. filtrationThe resulting solid was collected by filtration
  4. customdried at reduced pressure

Sources & evidence

ORD record
ord-2163b878118b4730aaa515d2f64ed6ed
Source dataset
uspto-grants-2012_01
Patent number
US08088767B2

Reaction notes

Loading…