Dibenamine hydrochloride → alpha-(N,N-dibenzylaminoethyl) benzyl cyanide

HRID 1612882

Reaction equation

[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Cl.Cl[CH2:22][CH2:23][N:24]([CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1COCC1>[CH2:32]([N:24]([CH2:23][CH2:22][CH:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Benzyl cyanide (0.97 mL, 8.4 mmole) was reacted with lithium bis(trimethylsilyl)amide (LHMDSA) (8.4 mL, 8.4 mmole) in 5 mL of THF at -78° C. for 1 hour. After an additional aliquot of LHMDSA (4.2 mL, 4.2 mmole) was added, N-(2-chloroethyl)dibenzylamine hydrochloride (1.0 g, 3.4 mmole) was then added. The reaction was allowed to stand at room temperature and was then warmed to 50° C. for 3.5 hours. The mixture was poured into ice/water, and the product was extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford alpha-(N,N-dibenzylaminoethyl) benzyl cyanide (1.05 g), isolated in 94% yield (MS: (M+H)+ =341).

Workup

additionAfter an additional aliquot of LHMDSA (4.2 mL, 4.2 mmole) was added
customto stand at room temperature
extractionthe product was extracted with ethyl acetate
washThe ethyl acetate layer was washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-c8eeb9d2ead14d3bbc0fb1dc636b3199
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05190922

Linked notes

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