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

HRID 2396135Notes

Reaction equation

HRID 2396135 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 kith 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 2M sodium carbonate solution. After washing the ethyl acetate layer kith water and drying kithsodium sulfate the solvent is evaporated. Recrystallization from toluene gives 27,2 g (73%) of the product having m.p. 135°-9° C.

Workup

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

Sources & evidence

ORD record
ord-1e00268a0a5e46968d0ae35200562364
Source dataset
uspto-grants-1996_02
Patent number
US05491173

Reaction notes

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