N,N-Diethyl-1-heptanamine → N,N-Diethyl-4-(2-chlorophenyl)-N-heptyl-2-buten-1-aminium chloride

HRID 464031Notes

Reaction equation

HRID 464031 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]=[CH:10][CH2:11]Cl.[CH2:13]([N:15]([CH2:23][CH3:24])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH3:14]>O>[Cl-:1].[CH2:23]([N+:15]([CH2:13][CH3:14])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:11][CH:10]=[CH:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])[CH3:24]

Participants

4

Reactant 2

HCID 12496130N,N-Diethyl-1-heptanamineHCID 544640551-Chloro-2-(4-chlorobut-2-en-1-yl)benzene

Product 1

HCID 70446502N,N-Diethyl-4-(2-chlorophenyl)-N-heptyl-2-buten-1-aminium chloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Combine 1.00 g (4.76 mmole) 1-chloro-2-(4-chloro-2- butenyl)benzene and 1.77 g (4.76 mmole) N,N-diethylheptanamine and heat at 100° C. ca. 20 hrs. Follow the progress of the reaction by TLC on silica gel (acetonitrile: ammonium hydroxide, 9:1). At the completion of the reaction, decant off the top layer of the two phase reaction mixture. Dissolve the bottom layer in 50 ml H2O. Extract with 3×100 ml hexane, 1×25 ml CH2Cl2. Dry CH2Cl2 over MgSO4 and treat with activated charcoal. Evaporate the solvents to provide the title compound.

Workup

  1. customthe progress of the reaction by TLC on silica gel (acetonitrile: ammonium hydroxide, 9:1)
  2. customAt the completion of the reaction
  3. customdecant off
  4. customthe top layer of the two phase reaction mixture
  5. extractionExtract with 3×100 ml hexane, 1×25 ml CH2Cl2
  6. additionDry CH2Cl2 over MgSO4 and treat with activated charcoal
  7. customEvaporate the solvents

Sources & evidence

ORD record
ord-4dfa644fbbcb4c75bc82df0fe89c77a6
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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