Benzaldehyde → HCID 73676366, compound

HRID 371750Notes

Reaction equation

HRID 371750 reaction equation
[C:1]12([CH2:10][NH2:11])[C:7]([CH3:9])([CH3:8])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[CH:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.O>C1(C)C=CC=CC=1>[CH:12](=[C:10]([NH2:11])[C:1]12[C:7]([CH3:8])([CH3:9])[CH:4]([CH2:5][CH2:6]1)[CH2:3][CH2:2]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 962WaterHCID 20356306HCID 20356306, compound

Product 1

HCID 73676366HCID 73676366, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

10-Bornanamine (824mg) in toluene (20ml) was treated with benzaldehyde (0.55ml) and the solution refluxed under nitrogen under a Dean and Stark water trap for four days. Evaporation of the solvent in vacuo afforded impure 10-benzylidene-10-bornanamine which was dissolved in dimethoxyethane (10ml) containing lithium aluminium hydride (112mg.). The resulting mixture was refluxed for 2.25 hours, cooled, and the excess hydride decomposed by the addition of water. The precipitated inorganic material was removed by filtration and the solvent was evaporated in vacuo. The residual gum was triturated with 2N-hydrochloric acid to afford an insoluble hydrochloride which was collected by filtration and then partitioned between ether and 2N-sodium hydroxide. The dried ethereal layer was evaporated in vacuo to give a yellow oil which was dissolved in ether and treated with ethanolic hydrogen chloride. The precipitated solid was collected and recrystallized from water to give title compound m.p. 310° (Found: C, 72.65; H, 9.65; Cl, 13.3; N, 4.95. C17H26ClN requires C, 72.95; H, 9.35; Cl, 12.65; N, 5.0%).

Workup

  1. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-24230c3497ee4e1e9a555008adceac83
Source dataset
uspto-grants-1978_05
Patent number
US04087551

Reaction notes

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