Methylamine → 1,2-diphenyl-1-[4-[2-(N-methylamino)ethoxy]phenyl]-1-buten-4-ol

HRID 982443Notes

Reaction equation

HRID 982443 reaction equation
[C:1]1(/[C:7](/[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26]Br)=[CH:20][CH:19]=2)=[C:8](/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)\[CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:28][NH2:29]>C(O)C>[C:1]1([C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][NH:29][CH3:28])=[CH:20][CH:19]=2)=[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][CH2:10][OH:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 69544510Z-1,2-diphenyl-1-[4-(bromoethoxy)phenyl]-1-buten-4-ol

Product 1

HCID 542527341,2-diphenyl-1-[4-[2-(N-methylamino)ethoxy]phenyl]-1-buten-4-olYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

42.3 g of (Z)-1,2-diphenyl-1-[4-(2-bromoethoxy)phenyl]-1-buten-4-ol is stirred over 500 ml of 33% methylamine in ethanol for 10 h at 100° C. in autoclave. The solvent is evaporated and the evaporation residue is dissolved in ethyl acetate in the presence of 2 M sodium carbonate solution. After washing the ethyl acetate layer with water and drying with sodium sulfate the solvent is evaporated. Recrystallization from toluene gives 27.2 g (73%) of the product having m.p. 134°-9° C.

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe evaporation residue is dissolved in ethyl acetate in the presence of 2 M sodium carbonate solution
  3. washAfter washing the ethyl acetate layer with water
  4. dry with materialdrying with sodium sulfate the solvent
  5. customis evaporated
  6. customRecrystallization from toluene

Sources & evidence

ORD record
ord-303fe089d18746bca68f7deeb58af049
Source dataset
uspto-grants-1991_02
Patent number
US04996225

Reaction notes

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