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

HRID 1168315Notes

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 48) 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 and then 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-b6e0467d61d1457788c8cd1d9ffcd0f3
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06624158B2

Reaction notes

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