Dimethyl Sulfoxide → N,N-dimethyl-1-(4-nitrophenyl)piperidin-4-amine

HRID 1804698

Reaction equation

HRID 1804698 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.CS(C)=O.[CH3:15][N:16]([CH3:23])[CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)CC)C>O>[CH3:15][N:16]([CH3:23])[CH:17]1[CH2:22][CH2:21][N:20]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 9590p-FluoronitrobenzeneHCID 417391N,N-Dimethylpiperidin-4-amine

Product 1

HCID 11086151N,N-dimethyl-1-(4-nitrophenyl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A 100 ml flask was charged with 1-fluoro-4-nitrobenzene (2.122 ml, 20 mmol), dimethylsulfoxide (30 ml), N,N-dimethylpiperidin-4-amine (2.82 g, 22.00 mmol) and triethylamine (5.58 ml, 40.0 mmol). The resulting solution was stirred at 100° C. under nitrogen for 24 hours. The reaction mixture was allowed to cool, and was poured in stirring cold water (1000 ml) and the solid collected by filtration and washed with water. The precipitate was vacuum dried to provide the title compound. MS (ESI(+)) m/e 249.9 (M+H)+.

Workup

  1. temperatureto cool
  2. additionwas poured
  3. filtrationthe solid collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-4067e18b2f174e3698967972cf5b3095
Source dataset
uspto-grants-2013_01
Patent number
US08354422B2

Linked notes

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