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

HRID 897107Notes

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 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
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-35e7042441ab42a983cd7d306069b4f1
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06921753B2

Reaction notes

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