Water → 3-(3-([1,3]Dioxolan-2-yl)propylamino)-1-aminobutane

HRID 493907Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[CH2:12][CH2:13][CH2:14][NH:15][CH:16]([CH3:20])[CH2:17][C:18]#[N:19].O.[OH-].[Na+]>C(OCC)C>[O:7]1[CH2:11][CH2:10][O:9][CH:8]1[CH2:12][CH2:13][CH2:14][NH:15][CH:16]([CH3:20])[CH2:17][CH2:18][NH2:19]

Participants

Conditions

Temperature: 35 °C

Procedure

In a 1.5 liter sulfonating flask, 10.7 g (0.282 mol) of lithium aluminium hydride are suspended in 620 ml of diethyl ether. Then 55.9 g (0.282 mol) of 3-(3-[1,3]dioxolan-2-yl-propylamino)butyronitrile in solution in 210 ml of diethyl ether are slowly added dropwise. The mixture is subsequently heated at 35° C. for three hours. After cooling to 0° C., 10.7 g of water, 10.7 g of 10% strength NaOH and then a further 32.1 g of water are carefully added dropwise. The reaction solution is filtered over Hyflo and concentrated under reduced pressure. This gives 49.86 g of 3-{3-([1,3]dioxolan-2-yl)propylamino}-1-aminobutane as a reddish liquid which is used without further purification in the next stage.

Workup

temperatureAfter cooling to 0° C.
filtrationThe reaction solution is filtered over Hyflo
concentrationconcentrated under reduced pressure
customThis gives 49.86 g of 3-{3-([1,3]dioxolan-2-yl)propylamino}-1-aminobutane as a reddish liquid which is used without further purification in the next stage

Sources & evidence

ORD record: ord-b1739d45db074ed388a876d5fd5056a5
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07538104B2

Reaction notes

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