Acetone → [(2-Nitrophenyl)methyl](propan-2-yl)amine

HRID 458225Notes

Reaction equation

HRID 458225 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH2:7][NH2:8])([O-:4])=[O:3].[CH3:13][C:14]([CH3:16])=O.C([BH3-])#N.[Na+]>CO>[CH:14]([NH:8][CH2:7][C:6]1[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=1[N+:2]([O-:4])=[O:3])([CH3:16])[CH3:13]

Participants

5

Reactant 3

HCID 180AcetoneHCID 5003444Sodium cyanoborohydrideHCID 12235442(2-Nitrophenyl)methanamine hydrochloride

Product 1

HCID 11608084[(2-Nitrophenyl)methyl](propan-2-yl)amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 2-nitrobenzylamine hydrochloride (500 mg, 2.65 mmol) and acetone (0.39 ml, 5.30 mmol) in methanol (13 ml) was added sodium cyanoborohydride (500 mg, 7.95 mmol) at 0° C. The temperature was warm up to room temperature. After stirring for 3 hr, the mixture was concentrated in vacuo and extracted with dichloromethane. The combined organic phase was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give N-isopropyl-2-nitrobenzylamine as yellow oil. This compound was used in next step without further purification.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. extractionextracted with dichloromethane
  3. washThe combined organic phase was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-849ac9a8e3f648d48ead1a6e600c07a8
Source dataset
uspto-grants-2007_03
Patent number
US07189858B2

Reaction notes

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