1-Bromopropane → HCID 67090312, compound

HRID 2075293Notes

Reaction equation

HRID 2075293 reaction equation
[CH3:1][N:2]([CH2:9][CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br:11][CH2:12][CH2:13][CH3:14]>C(#N)C>[Br-:11].[CH2:12]([N+:2]([CH3:1])([CH2:9][CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)[CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 78401-BromopropaneHCID 11956Benzenamine, N-ethyl-N-methyl-

Product 1

HCID 67090312HCID 67090312, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 mmol of N-methyl-N-ethylaniline (Aldrich) were quaternized with 100 mmol of bromopropane (Aldrich) at reflux in 100 ml of acetonitrile for 48 hours. After evaporation of the solvent, the N-propyl-N-methyl-N-ethylanilinium bromide (PMEA.Br) obtained was purified by washing with ether. 50 mmol of KBFST were added to 50 mmol of PMEA.Br in 100 ml of water, and then the solution was extracted with twice 50 ml of dichloromethane. After evaporation of the solvent and drying under vacuum, PMEA.BFST was obtained. The two optical isomer forms of this salt were separated on a chiral column. The two optical isomers isolated serve as a chiral reaction medium.

Workup

  1. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-41903f42d8df420aaec451e9b0513004
Source dataset
uspto-grants-2011_04
Patent number
US07919629B2

Reaction notes

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