Isopropylamine → 2-{[(Propan-2-yl)amino]methyl}aniline

HRID 583065Notes

Reaction equation

HRID 583065 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-])=O.[CH:12]([NH2:15])([CH3:14])[CH3:13]>CO.[Pd]>[NH2:1][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][NH:15][CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 2

HCID 6363IsopropylamineHCID 111012-Nitrobenzaldehyde

Product 1

HCID 144939632-{[(Propan-2-yl)amino]methyl}aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a 500 ml 3-necked round bottom flask equipped with overhead mechanical stirrer, thermometer and nitrogen bubbler was charged 2-nitrobenzaldehyde (200 g, 1.32 mol) in methanol (1300 ml), to which was added isopropylamine (78.0 g, 113 ml, 1.32 mol) in one portion with stirring under nitrogen. The reaction mixture was then stirred for 100 minutes (followed reaction by GC), then added to a 4 litre stainless steel Parr hydrogenator, containing a suspension of 5% palladium on charcoal (13.24 g, 6% cat. loading) in methanol (500 ml) and the suspension hydrogenated under hydrogen at 60 psi for 3 hours. The suspension was filtered through a pad of celite, the pad washed with methanol (500 ml) and the combined filtrate evaporated under reduced pressure to leave a yellow oil, 2-amino-N-(1-methylethyl)-benzylamine.

Workup

  1. customTo a 500 ml 3-necked round bottom flask equipped with overhead mechanical stirrer
  2. stirringThe reaction mixture was then stirred for 100 minutes
  3. custom(followed reaction by GC)
  4. additioncontaining
  5. filtrationThe suspension was filtered through a pad of celite
  6. washthe pad washed with methanol (500 ml)
  7. customthe combined filtrate evaporated under reduced pressure

Sources & evidence

ORD record
ord-6123a4c1db7a40c78a56b0cd705100ce
Source dataset
uspto-grants-1999_07
Patent number
US05929072

Reaction notes

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