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

HRID 277998Notes

Reaction equation

HRID 277998 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 p.s.i. 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. MS (FD+) (m/e): 146.

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-720a3c0dc19a459f94cd736d115f9ba1
Source dataset
uspto-grants-2002_03
Patent number
US06358972B1

Reaction notes

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