Diethylamine → (E)-4-(4-Chlorophenyl)-N,N-diethyl-2-buten-1-amine

HRID 464025Notes

Reaction equation

HRID 464025 reaction equation
[CH2:1]([NH:3][CH2:4][CH3:5])[CH3:2].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]/[CH:14]=[CH:15]/[CH2:16]Cl)=[CH:9][CH:8]=1.ClC1C=CC(CC(Cl)C=C)=CC=1>Cl>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13]/[CH:14]=[CH:15]/[CH2:16][N:3]([CH2:4][CH3:5])[CH2:1][CH3:2])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 12616294(E)-1-chloro-4-(4-chloro-2-butenyl)benzeneHCID 136602341-Chloro-4-(2-chloro-3-butenyl)benzene

Product 1

HCID 20263609(E)-4-(4-Chlorophenyl)-N,N-diethyl-2-buten-1-amine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Add 30 ml diethylamine to 10.0 g (0.05 mole) of a 7:3 mixture of (E)-1-chloro-4-(4-chloro-2-butenyl)benzene and 1-chloro-4-(2-chloro-3-butenyl)benzene and stir at room temperature overnight. Dissolve reaction mixture in 100 ml 1N HCl and wash with 50 ml ethyl acetate. Extract ethyl acetate layer with 50 ml 1N HCl. Combine aqueous layers and add cold 4N NaOH until solution has pH=9. Extract aqueous phase with 5×60 ml Et2O. Dry ethereal extracts over Na2SO4 and then filter. Evaporate solvent to provide the title compound.

Workup

  1. dissolutionDissolve
  2. washwash with 50 ml ethyl acetate
  3. additionCombine aqueous layers and add cold 4N NaOH until solution
  4. dry with materialDry ethereal extracts over Na2SO4
  5. filtrationfilter

Sources & evidence

ORD record
ord-24b85db2c74244f8ac520934d23f4f98
Source dataset
uspto-grants-1985_10
Patent number
US04545995

Reaction notes

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