Ammonia → Z-1,2-diphenyl-1-[4-(2-aminoethoxy)phenyl]-1-buten-4-ol

HRID 2396136Notes

Reaction equation

HRID 2396136 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.[NH3:28]>C(O)C>[C:1]1(/[C:7](/[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][NH2:28])=[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 222AmmoniaHCID 69544510Z-1,2-diphenyl-1-[4-(bromoethoxy)phenyl]-1-buten-4-ol

Product 1

HCID 67771823Z-1,2-diphenyl-1-[4-(2-aminoethoxy)phenyl]-1-buten-4-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

10.0 g of Z-1,2-diphenyl-1-[4-(bromoethoxy)phenyl]-1-buten-4-ol is added to200 ml of ethanol saturated with ammonia gas. The solution is stirred for 3hours at 90° C. in an autoclave. The solvent is evaporated and the residue is dissolved in ethyl acetate in the presence of 2M sodium hydroxide solution by warming the solution on a water bath. The organic layer is washed with water. The precipitated product is filtered off. The yield is 5.1 g (60%).

Workup

  1. customThe solvent is evaporated
  2. dissolutionthe residue is dissolved in ethyl acetate in the presence of 2M sodium hydroxide solution
  3. temperatureby warming the solution on a water bath
  4. washThe organic layer is washed with water
  5. filtrationThe precipitated product is filtered off

Sources & evidence

ORD record
ord-3ecfac320443437d837999994cad76ad
Source dataset
uspto-grants-1996_02
Patent number
US05491173

Reaction notes

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