Dimethylamine → 3-(4-Chlorophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amine

HRID 1649547Notes

Reaction equation

HRID 1649547 reaction equation
C1(P(C2C=CC=CC=2)CCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O[C:33]([C:42]1[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=1)([C:36]1[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=1)[CH:34]=[CH2:35])(=O)C.[CH3:49][NH:50][CH3:51]>O1CCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Pd+2]>[Cl:48][C:45]1[CH:46]=[CH:47][C:42]([C:33]([C:36]2[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=2)=[CH:34][CH2:35][N:50]([CH3:51])[CH3:49])=[CH:43][CH:44]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 742671,2-Bis(diphenylphosphino)ethaneHCID 127171053-Acetoxy-3-(4-chlorophenyl)-3-(3-pyridyl)-1-propene

Product 1

HCID 542523273-(4-Chlorophenyl)-N,N-dimethyl-3-(pyridin-3-yl)prop-2-en-1-amineYield 79%

Reagents, catalysts & solvents 2

HCID 5486778Palladium acetylacetonateCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

Palladium acetylacetonate (9.3 mg, 0.03 mmol), 1,2-bis-(diphenylphosphino)ethane (17.5 mg, 0.04 mmol) and 3-acetoxy-3-(4-chlorophenyl)-3-(3-pyridyl)-1-propene (0.211 g, 0.73 mmol) was dissolved in tetrahydrofuran (2.2 ml) at room temperature under nitrogen. A solution of dimethylamine in tetrahydrofuran (3.2 ml of a 2.5 M solution) was added. The resulting solution was warmed to 55° C. and allowed to react for 1 h and 40 min. Evaporation of the solvent and work-up by preparative TLC (SiO2, ethyl acetate/hexane/triethylamine 49/49/2) gave 0.158 g (79%) of a Z/E mixture of the title compound. The Z/E ratio was determined by 1H NMR to 55/45.

Workup

  1. customto react for 1 h and 40 min
  2. customEvaporation of the solvent

Sources & evidence

ORD record
ord-f1a58352df91489aae5ccb61bd09138d
Source dataset
uspto-grants-1983_11
Patent number
US04418065

Reaction notes

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