Ethylamine → N-ethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine

HRID 2423225Notes

Reaction equation

HRID 2423225 reaction equation
[CH3:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)([CH3:5])[CH:3]=O.[CH2:15]([NH2:17])[CH3:16].[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[CH2:15]([NH:17][CH2:3][C:2]([CH3:5])([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)[CH3:1])[CH3:16]

Participants

6

Reactant 3

HCID 6341EthylamineHCID 4311764Sodium borohydrideHCID 15074483HCID 15074483, compound

Product 1

HCID 67243335N-ethyl-2-methyl-2-(4-nitrophenyl)propan-1-amineYield 98%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL round bottom flask was charged 2-methyl-2-(4-nitrophenyl)propanal (2.00 g, 10.4 mmol), absolute ethanol (30 mL), ethyl amine solution (20.7 mL, 1M in THF). Titanium isopropoxide (6.2 mL, 20.7 mmol) was added and the mixture was stirred at ambient temperature for 1 h. Sodium borohydride (1.17 g, 31 mmol) was added and the reaction stirred for an additional 1 h. The reaction was quenched by pouring into 10% ammonium hydroxide solution (25 mL), ethyl acetate was added and the solids were removed by filtration, the pad was washed once with ethyl acetate and the solvent was concentrated in vacuo to give N-ethyl-2-methyl-2-(4-nitrophenyl)propan-1-amine (2.25 g, 98%). LC/MS (ESI+) 223 (M+H)+.

Workup

  1. stirringthe reaction stirred for an additional 1 h
  2. customThe reaction was quenched
  3. additionby pouring into 10% ammonium hydroxide solution (25 mL), ethyl acetate
  4. additionwas added
  5. customthe solids were removed by filtration
  6. washthe pad was washed once with ethyl acetate
  7. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-398234dfd7dd4d3a9b4c31a809b6e441
Source dataset
uspto-grants-2011_06
Patent number
US07960569B2

Reaction notes

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