2-Methyl-2-(3-nitropropyl)-1,3-dioxolane → 3-(2-Methyl-1,3-dioxolan-2-yl)-1-propanamine

HRID 2084626Notes

Reaction equation

HRID 2084626 reaction equation
[N+:1]([CH2:4][CH2:5][CH2:6][C:7]1([O:12][CH2:11][CH2:10][O:9]1)[CH3:8])([O-])=O>CO>[NH2:1][CH2:4][CH2:5][CH2:6][C:7]1([O:12][CH2:11][CH2:10][O:9]1)[CH3:8]

Participants

3

Reactant 1

HCID 6383462-Methyl-2-(3-nitropropyl)-1,3-dioxolane

Product 1

HCID 5600073-(2-Methyl-1,3-dioxolan-2-yl)-1-propanamineYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Nitro-2,2-ethylenedioxypentane (103 g) is dissolved in methanol (2.0 l) and initially introduced into a hydrogenation flask. After the thorough flushing of the apparatus with N2, 10% Pd/C (10 g) is added. Hydrogenation is then carried out at RT under normal conditions in a stream of H2 for a total of 11 h with vigorous stirring. After the reaction is complete (TLC dichloromethane/methanol=9:1, staining reagent 1.0% strength ethanolic ninhydrin solution), the flask is flushed with N2 and the mixture is filtered off with suction through kieselguhr. The colorless filtrate is concentrated to dryness at T≦40° C. and p≧30 mbar, the title compound (85 g, quant.) first being obtained as a colorless oil, which solidifies to give a wax. TLC (dichloromethane/methanol=9:1), Rf=0.0 -0.22.

Workup

  1. additioninitially introduced into a hydrogenation flask
  2. customAfter the thorough flushing of the apparatus with N2, 10% Pd/C (10 g)
  3. additionis added
  4. customis then carried out at RT under normal conditions in a stream of H2 for a total of 11 h with vigorous stirring
  5. customthe flask is flushed with N2
  6. filtrationthe mixture is filtered off with suction through kieselguhr
  7. concentrationThe colorless filtrate is concentrated to dryness at T≦40° C. and p≧30 mbar

Sources & evidence

ORD record
ord-d148b1afa020495a898a5e1228549591
Source dataset
uspto-grants-2004_04
Patent number
US06716990B2

Reaction notes

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