Water → 4-(3-Amino-4-nitrophenyl)-1-piperazineethanol

HRID 1465824Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([CH:8]=1)[NH2:7].[N:12]1([CH2:18][CH2:19][OH:20])[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C>[NH2:7][C:6]1[CH:8]=[C:2]([N:15]2[CH2:16][CH2:17][N:12]([CH2:18][CH2:19][OH:20])[CH2:13][CH2:14]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 122.5 °C

Procedure

A mixture of 5-chloro-2-nitroaniline (5.0 g, 29.0 mmol), 2-piperazin-1-yl-ethanol (11.3 g, 87.0 mmol) and anhydrous potassium carbonate (4.4 g, 31 mmol) in N,N-dimethylacetamide (10 ml) was stirred at 120-125° C. under nitrogen for 1 day. Sample NMR analysis showed complete conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water (30 ml) and stirred vigorously and cooled at 5° C. overnight. The resulting yellow precipitate was collected by filtration, washed well with water then dried on the filter funnel. The resulting yellow brown solid was slurried in diethyl ether (30 mL), filtered, washed with additional diethyl ether, dried to afford 2-[4-(3-Amino-4-nitro-phenyl)-piperazin-1-yl]-ethanol (6.0 g, 77%) as a yellow powder.

Workup

stirringstirred vigorously
temperaturecooled at 5° C. overnight
filtrationThe resulting yellow precipitate was collected by filtration
washwashed well with water
customthen dried on the filter funnel
filtrationfiltered
washwashed with additional diethyl ether
customdried

Sources & evidence

ORD record: ord-0a87f06c1bc04040a5722a9dfdaef95a
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999993B2

Reaction notes

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