HCID 12822287, compound → HCID 12822291, compound

HRID 1112276Notes

Reaction equation

HRID 1112276 reaction equation
C1(C([NH:9][CH2:10][CH:11]2[CH2:15][O:14][C:13](=[O:16])[C:12]2([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)C)C=CC=CC=1.[H][H]>[OH-].[Pd+2].[OH-].CO>[OH:14][CH2:15][CH:11]1[CH2:10][NH:9][C:13](=[O:16])[C:12]1([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 12822287HCID 12822287, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 12822291HCID 12822291, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To 750 ml. of methanol and 80.0 g. (0.22 mole) of 4-(1-phenylethylaminomethyl)-4,5-dihydro-3,3-diphenylfuran-2(3H)one was added 3.0 g. of palladium hydroxide catalyst and the mixture was shaken in 3 atmospheres of hydrogen at 70° C. for 18 hrs. Upon filtering starting material was found to be present; fresh catalyst was added to the solution which was shaken in 3 atmospheres of hydrogen at 70° C. for 3 more hours. After filtering the filtrate was concentrated in vacuo. The residue was dissolved in 100 ml. of ethyl acetate, and 100 ml. of isopropyl ether was added. A portion of the crystallized material was recrystallized from the same solvent system to give product melting at 145°-148° C.

Workup

  1. filtrationUpon filtering
  2. additionfresh catalyst was added to the solution which
  3. filtrationAfter filtering the filtrate
  4. concentrationwas concentrated in vacuo
  5. dissolutionThe residue was dissolved in 100 ml
  6. additionof isopropyl ether was added
  7. customA portion of the crystallized material was recrystallized from the same solvent system

Sources & evidence

ORD record
ord-dc042be5490242018d2aa781d3fef9db
Source dataset
uspto-grants-1978_10
Patent number
US04120969

Reaction notes

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