HCID 21281919, compound → HCID 70417539, compound

HRID 414246Notes

Reaction equation

HRID 414246 reaction equation
[CH3:1][CH:2]([O:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24]4[CH:29]=[CH:28][C:27]([O:30]CC5C=CC=CC=5)=[CH:26][CH:25]=4)[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)[C:8]1=[O:38])[CH3:3].[H][H]>[Pd].C(O)(=O)C>[OH2:4].[OH:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[CH2:20][CH2:19][N:18]([C:15]3[CH:14]=[CH:13][C:12]([N:9]4[CH2:10][CH2:11][N:7]([CH2:6][CH2:5][O:4][CH:2]([CH3:1])[CH3:3])[C:8]4=[O:38])=[CH:17][CH:16]=3)[CH2:23][CH2:22]2)=[CH:25][CH:26]=1.[OH:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[CH2:20][CH2:19][N:18]([C:15]3[CH:14]=[CH:13][C:12]([N:9]4[CH2:10][CH2:11][N:7]([CH2:6][CH2:5][O:4][CH:2]([CH3:1])[CH3:3])[C:8]4=[O:38])=[CH:17][CH:16]=3)[CH2:23][CH2:22]2)=[CH:25][CH:26]=1

Participants

5

Reactant 2

HCID 21281919HCID 21281919, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70417539HCID 70417539, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 9.7 parts of 1-[2-(1-methylethoxy)ethyl]-3-[4-[4-[4-(phenylmethoxy)phenyl]-1-piperazinyl]phenyl]-2-imidazolidinone and 250 parts of acetic acid was hydrogenated at normal pressure and at 50° C. with 2 parts of palladium-on-charcoal catalyst 10%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The residue was dissolved in a mixture of methanol and water and the whole was neutralised with a sodium hydrogen carbonate solution. The precipitated product was filtered off and crystallized from 4-methyl-2-pentanone. The product was filtered off and dried at 100° C., yielding 6.3 parts (76.8%) of 1-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-3-[2-(1-methylethoxy)ethyl]-2-imidazolidinone hemihydrate; mp. 178.3° C. (intermediate 28).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in a mixture of methanol and water
  4. filtrationThe precipitated product was filtered off
  5. customcrystallized from 4-methyl-2-pentanone
  6. filtrationThe product was filtered off
  7. customdried at 100° C.

Sources & evidence

ORD record
ord-3e0d4439f138405eaf0e892ed2e00da3
Source dataset
uspto-grants-1988_12
Patent number
US04791111

Reaction notes

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