Carbon Tetrachloride → 4-chloro-1,2-diphenyl-1-[4-[2-(N-methylamino)ethoxy]phenyl]1-butene

HRID 982444Notes

Reaction equation

HRID 982444 reaction equation
Cl.[C:2]1(/[C:8](/[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][NH:28][CH3:29])=[CH:21][CH:20]=2)=[C:9](/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)\[CH2:10]CO)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49]([Cl:53])(Cl)(Cl)Cl>C(#N)C>[Cl:53][CH2:49][CH2:10][C:9]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[C:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][NH:28][CH3:29])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 67944775(Z)-1,2-diphenyl-1-[4-[2-(N-methylamino)ethoxy]phenyl]-1-buten-4-ol hydrochloride

Product 1

HCID 1193444-chloro-1,2-diphenyl-1-[4-[2-(N-methylamino)ethoxy]phenyl]1-butene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture containing 41.0 g of (Z)-1,2-diphenyl-1-[4-[2-(N-methylamino)ethoxy]phenyl]-1-buten-4-ol hydrochloride, 57.4 g of triphenyl phosphine, 61.6 g of carbon tetrachloride and 500 ml of acetonitrile is refluxed for 1 h. On cooling the product crystallizes out and is collected for filtration. The yield of the hydrochloride is 25.3 g (59%) and m.p. 206°-8° C. The base is liberated from its salt by conventional means giving an oil.

Workup

  1. temperatureis refluxed for 1 h
  2. temperatureOn cooling the product
  3. customcrystallizes out
  4. filtrationis collected for filtration
  5. customgiving an oil

Sources & evidence

ORD record
ord-c61b0e4e795d4aa1bb539ba9ef93b869
Source dataset
uspto-grants-1991_02
Patent number
US04996225

Reaction notes

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