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

HRID 1293039Notes

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 39) 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 was 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 was slurried with diethyl ether (200 ml) for 30 minutes
filtrationfiltered
customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record: ord-e0e26b934f34481e95c87faf77ca1518
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238676B2

Reaction notes

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