Water → N1-Cyclopentyl-N1-isopropylethane-1,2-diamine

HRID 10450Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([N:12]([CH2:16][C:17]#[N:18])[CH:13]([CH3:15])[CH3:14])[CH2:11][CH2:10][CH2:9][CH2:8]1.[OH-].[Na+].O>O1CCCC1>[CH:7]1([N:12]([CH:13]([CH3:15])[CH3:14])[CH2:16][CH2:17][NH2:18])[CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminium hydride (66 ml of a 1 molar solution in tetrahydrofuran, 0.066 mol) was added to a stirred solution of [cyclopentyl(isopropyl)amino]acetonitrile (10 g, 0.66 mol) (Preparation 24) in tetrahydrofuran (100 ml) at 0° C. The reaction mixture was stirred at 0° C. for 20 minutes and then heated under reflux for 2 hours. The reaction mixture was allowed to cool to room temperature and left to stand overnight. The reaction mixture was cooled in an icebath and treated dropwise with 4.8 ml of a 7.5% w/w aqueous sodium hydroxide solution followed by 7.4 ml of water. The solvent was removed under reduced pressure and the residue slurried with diethyl ether (200 ml) for 30 minutes and then filtered. The filtrate was evaporated under reduced pressure to give the title compound as a colourless oil (10.30 g).

Workup

temperatureheated
temperatureunder reflux for 2 hours
temperatureto cool to room temperature
waitleft
waitto stand overnight
temperatureThe reaction mixture was cooled in an icebath
customThe solvent was removed under reduced pressure
waitthe residue slurried with diethyl ether (200 ml) for 30 minutes
filtrationfiltered
customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-6a39682c48824103b1827335e43915c2
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07094769B2

Reaction notes

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