Dibenzylamine → (E)-N,N-Dibenzyl-3-phenylprop-2-en-1-amine

HRID 1627957Notes

Reaction equation

HRID 1627957 reaction equation
[CH2:1](OC1C=CC=CC=1)[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:17]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:25]([N:24]([CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:1]/[CH:2]=[CH:3]/[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 7656DibenzylamineHCID 258010Cinnamyloxybenzene

Product 1

HCID 9944644(E)-N,N-Dibenzyl-3-phenylprop-2-en-1-amineYield 93%

Procedure

Following the general procedure using cinnamyloxybenzene (105 mg, 0.50 mmol) and dibenzylamine (148 mg, 0.75 mmol), the reaction was stirred for 0.5 h at rt. Column chromatography on silica gel (eluting with 8% EtOAc/hexanes) afforded the product as a pale yellow liquid (145 mg, 93%).

Sources & evidence

ORD record
ord-9d99684539ab40b09f64d2b6f5687328
Source dataset
uspto-grants-2014_07
Patent number
US08785665B2

Reaction notes

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