Diisopropylethylamine → 1-(3-methoxy-4-nitrophenyl)-N,N-dimethylpiperidin-4-amine

HRID 42267

Reaction equation

HRID 42267 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.[CH3:13][N:14]([CH3:21])[CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1.C(N(C(C)C)C(C)C)C>CN(C)C=O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:18]2[CH2:19][CH2:20][CH:15]([N:14]([CH3:21])[CH3:13])[CH2:16][CH2:17]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 417391N,N-Dimethylpiperidin-4-amineHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 574161521-(3-methoxy-4-nitrophenyl)-N,N-dimethylpiperidin-4-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-fluoro-2-methoxy-1-nitrobenzene (1.711 g, 10 mmol), N,N-dimethylpiperidin-4-amine (1.410 g, 11.00 mmol) and N-ethyl-N-isopropylpropan-2-amine (3.48 mL, 20.00 mmol) in anhydrous N,N-dimethylformamide (25 mL) was stirred at 70° C. overnight. The mixture was concentrated and the residue was mixed with water (60 mL), adjusted to pH 12, then extracted with CH2Cl2. The crude product was purified on a silica gel column eluting with 7.5% methanol in CH2Cl2 saturated with NH3 to provide the title compound. (ESI+) m/e 280.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was mixed with water (60 mL)
  3. extractionextracted with CH2Cl2
  4. customThe crude product was purified on a silica gel column
  5. washeluting with 7.5% methanol in CH2Cl2 saturated with NH3

Sources & evidence

ORD record
ord-65c1901d151e45e48f0b1f53084003e2
Source dataset
uspto-grants-2013_09
Patent number
US08536180B2

Linked notes

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