2-(3-Cyanopropyl)-1,3-dioxolane → 2-(4-Aminobutyl)-1,3-dioxolane

HRID 363316Notes

Reaction equation

HRID 363316 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1)#[N:2].[H][H]>N.C(O)C.[Ru]>[NH2:2][CH2:1][CH2:3][CH2:4][CH2:5][CH:6]1[O:10][CH2:9][CH2:8][O:7]1

Participants

6

Reactant 2

HCID 146840292-(3-Cyanopropyl)-1,3-dioxolaneHCID 178418361HCID 178418361, compound

Product 1

HCID 226267802-(4-Aminobutyl)-1,3-dioxolaneYield 802.4%

Reagents, catalysts & solvents 3

HCID 23950RutheniumCatalystHCID 222AmmoniaSolventHCID 702EthanolSolvent

Procedure

To a solution of 14.5 gm (10.3 mmol) 2-(3-Cyanopropyl)-1,3-dioxolane in anhydrous ammonia and ethanol was added 5% ruthenium on aluminum oxide. The reaction mixture was hydrogenated with an initial hydrogen pressure of 100 psi at ambient temperature for 32 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure. The residue was purified by silica gel chromatography to give 12.0 gm (80.5%) of the product.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-cdd96a8012194a85bc076da0213f63a3
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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