Water → HCID 59452601, compound

HRID 419357Notes

Reaction equation

HRID 419357 reaction equation
Cl[C:2]1[C:3]([CH3:23])=[C:4]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[CH3:24][O-:25].[Na+].O>CN(C=O)C>[CH3:23][C:3]1[C:2]([O:25][CH3:24])=[C:7]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:5][C:4]=1[N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 59452868HCID 59452868, compound

Product 1

HCID 59452601HCID 59452601, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 1′-(3-chloro-2-methyl-4-nitrophenyl)-1,4′-bipiperidine (0.50 g, 1.5 mmol) in DMF (15 mL) was added sodium methoxide (0.97 g, 1.8 mmol) at 0° C., and the mixture was stirred at rt overnight. The mixture was poured into H2O, extracted with EtOAc, washed with H2O, dried and concentrated to provide the title compound of step B (0.53 g, 1.6 mmol, 100% crude). 1H NMR (400 MHz, CDCl3) δ ppm 1.41-1.50 (m, 2H), 1.61-1.71 (m, 4H), 1.70-1.81 (m, 2H), 1.91-2.01 (m, 2H), 2.25 (s, 3H), 2.35-2.45 (m, 1H), 2.51-2.60 (m, 4H), 2.65-2.75 (m, 2H), 3.21-3.30 (m, 2H), 3.9 (s, 3H), 6.75 (d, J=9.2 Hz, 1H), 7.75 (d, J=9.2 Hz, 1H).

Workup

  1. extractionextracted with EtOAc
  2. washwashed with H2O
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ad511348cf974f5f802eb4e5f65269d3
Source dataset
uspto-grants-2012_01
Patent number
US08093239B2

Reaction notes

Loading…