Water → HCID 30772162, compound

HRID 2400755Notes

Reaction equation

HRID 2400755 reaction equation
C(N(CC)CC)C.Cl[C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17].[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].O>CS(C)=O>[C:19]([O:23][C:24]([N:26]1[CH2:31][CH2:30][N:29]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[N+:16]([O-:18])=[O:17])[CH2:28][CH2:27]1)=[O:25])([CH3:22])([CH3:20])[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 118992,4-DichloronitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 30772162HCID 30772162, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
70 °C

Procedure

Triethylamine (4.2 ml) was added to a stirred solution of 2,4-dichloronitrobenzene (1.9 g) and 1-t-butoxycarbonyl-piperazine (2.2 g) in dimethylsulfoxide (18 ml) under N2. The resulting solution was stirred at 70° C. for 48 hours then cooled to room temperature. Water was added and the mixture extracted three times with ethyl acetate; the combined organic layers were dried over sodium sulfate and concentrated in vacuo. The residue was subjected to silica gel chromatography (cyclohexane:ethyl acetate 8:2) to afford 4-(5-chloro-2-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester (2.6 g) as a foam. 1H NMR (400 MHz, CDCl3) 1.5 (s, 9H), 2.9 (br s, 4H), 3.5 (br s, 4H), 6.9 (d, J=10 Hz, 1H), 7.0 (s, 1H), 7.7 (d, J=10 Hz, 1H); MS (ES+) 242/244 (M+H+—CO2-isobutene), 286/288 (M+H+-isobutene).

Workup

  1. temperaturethen cooled to room temperature
  2. extractionthe mixture extracted three times with ethyl acetate
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf39c24fc302455e969a7bd21d160396
Source dataset
uspto-grants-2014_08
Patent number
US08796274B2

Reaction notes

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