(E)-4-(4-Chlorophenyl)-N,N-diethyl-N-heptyl-2-buten-1-aminium chloride → 4-chloro-N,N-diethyl-N-heptylbenzenebutanaminium chloride

HRID 464034Notes

Reaction equation

HRID 464034 reaction equation
[Cl-].[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9]/[CH:10]=[CH:11]/[CH2:12][N+:13]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:5][CH:4]=1.[H][H]>C(O)(=O)C>[Cl-:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][N+:13]([CH2:23][CH3:24])([CH2:21][CH3:22])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 13660267(E)-4-(4-Chlorophenyl)-N,N-diethyl-N-heptyl-2-buten-1-aminium chlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 202636074-chloro-N,N-diethyl-N-heptylbenzenebutanaminium chloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Add 2.1 g (5.6 mmole) of (E)-4-(4-chlorophenyl)-N,N-diethyl-N-heptyl-2-buten-1-aminium chloride to a suspension of 0.11 g catalyst (rhodium (5%) on carbon) in 100 ml glacial acetic acid and stir under 1 atmosphere hydrogen for 19 hours at room temperature. Filter through celite and then wash celite with 100 ml H2O. Combine filtrates and extract into 4×100 ml methylene chloride. Wash methylene chloride extracts with 1×100 ml 1N HCl, 2×250 ml saturated aqueous sodium bicarbonate and 200 ml saturated aqueous sodium chloride. Dry methylene chloride over sodium sulfate, filter and evaporate solvent to provide 4-chloro-N,N-diethyl-N-heptylbenzenebutanaminium chloride. Dissolve product in 75 ml H2O/MeOH (50:50) and pour onto column containing 6 g anion exchange resin (hydroxide form BIO-RAD AG-1-X8). Elute sample through column with distilled water and collect eluate having pH≥9. Wash this aqueous solution with 2×150 ml methylene chloride. Titrate sample to pH= 5.0 with 10% phosphoric acid and to pH=4.5 with 0.1N phosphoric acid. Evaporate to provide 1.25 (51%) of title compound.

Workup

  1. filtrationFilter through celite
  2. washwash celite with 100 ml H2O
  3. extractionCombine filtrates and extract into 4×100 ml methylene chloride
  4. filtrationDry methylene chloride over sodium sulfate, filter
  5. customevaporate solvent

Sources & evidence

ORD record
ord-d2c4f47bd8524daa964615345e94d6b0
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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