Aluminium lithium hydride → N1,N1-diethyl-2,2-diphenylpropane-1,3-diamine

HRID 1685308Notes

Reaction equation

[CH2:1]([N:3]([CH2:20][CH3:21])[CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:6]#[N:7])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:20]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:6][NH2:7])[CH3:21]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 3-(diethylamino)-2,2-diphenylpropanenitrile (0.627 g, 2.25 mmol) in diethyl ether (5 mL) was slowly added to a suspension of lithium aluminum hydride (0.171 g, 4.50 mmol) in diethyl ether (5 mL) at 0° C. The resulting slurry was stirred at 0° C. for 1.5 hours. The reaction was then quenched by adding sodium sulphate decahydrate and stirring for 30 minutes. The reaction was then diluted with ethyl acetate and celite was added. The suspension was filtered and the filtrate was concentrated to dryness to give the title material (0.511 g, 80%) as an oil. LC/MS (M+H)+: 283. HPLC ret. time (Condition B): 1.602 min. 1H NMR (400 MHz, CDCl3) δ ppm: 0.81 (6H, t, J=7.07 Hz), 2.19 (4H, q, J=7.07 Hz), 3.18 (2H, s), 3.51 (2H, s) 7.16-7.20 (6H, m) 7.24-7.32 (4H, m).

Workup

customThe reaction was then quenched
additionby adding sodium sulphate decahydrate
stirringstirring for 30 minutes
additionThe reaction was then diluted with ethyl acetate and celite
additionwas added
filtrationThe suspension was filtered
concentrationthe filtrate was concentrated to dryness

Sources & evidence

ORD record: ord-a670714e3091433ca50bebe99cd351c2
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08148400B2

Reaction notes

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