Sodium Hydroxide → 3-(1-Methyl-4-piperidinyl)benzenamine

HRID 1275003Notes

Reaction equation

HRID 1275003 reaction equation
[I-].[CH3:2][N+:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=2)=[CH:5][CH:4]=1.[BH4-].[Na+].[OH-].[Na+]>C(O)C.O>[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:10]=[C:11]([CH:12]=[CH:13][CH:14]=2)[NH2:15])[CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 221189241-Methyl-4-(3-nitrophenyl)pyridin-1-ium iodide

Product 1

HCID 223301453-(1-Methyl-4-piperidinyl)benzenamineYield 94.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 1-methyl-4-(3-nitrophenyl)pyridinium iodide (D5, 4.0 g, 11.7 mmol) in ethanol (100 ml) and water (100 ml) at 0° C. was added sodium borohydride (665 mg, 17.6 mmol) portionwise over 0.5 h, before allowing to warm to room temperature while stirring for 2h. To the mixture was added 10% NaOH solution (100 ml) and the product extracted with dichloromethane (2×), dried (Na2SO4) and evaporated in vacuo to a brown oil (2.6 g). The oil was dissolved in ethanol (100 ml) and hydrogenated over 10% Pd--C at 50 psi and 50° C. for 48 h. Filtration and evaporation in vacuo of the filtrate gave the title compound as a yellow oil (2.1 g, 93%).

Workup

  1. extractionthe product extracted with dichloromethane (2×)
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo to a brown oil (2.6 g)
  4. dissolutionThe oil was dissolved in ethanol (100 ml) and hydrogenated over 10% Pd--C at 50 psi and 50° C. for 48 h
  5. filtrationFiltration and evaporation in vacuo of the filtrate

Sources & evidence

ORD record
ord-122f20013b104f2fb9c4e60c697e3458
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

Loading…