1,4-Dioxane → 3-[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]-1-(1-methylethyl)-2,4-imidazolidinedione

HRID 1723492Notes

Reaction equation

HRID 1723492 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:30])OC4C=CC=CC=4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH3:31][CH:32]([NH:34][CH2:35][C:36](OCC)=[O:37])[CH3:33].O1CCOCC1>CN(C)C1C=CN=CC=1.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:16]=[CH:17][C:18]([N:21]4[C:36](=[O:37])[CH2:35][N:34]([CH:32]([CH3:33])[CH3:31])[C:22]4=[O:30])=[CH:19][CH:20]=3)[CH2:13][CH2:14]2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 351625Ethyl 2-((propan-2-yl)amino)acetateHCID 981607Phenyl N-(4-(4-(4-methoxyphenyl)piperazin-1-yl)phenyl)carbamate

Product 1

HCID 141529353-[4-[4-(4-Methoxyphenyl)-1-piperazinyl]phenyl]-1-(1-methylethyl)-2,4-imidazolidinedioneYield 73%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

A mixture of 5 parts of phenyl [4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]carbamate, 3 parts of ethyl [(1-methylethyl)amino]acetate, 1 part of N,N-dimethyl-4-pyridinamine and 100 parts of 1,4-dioxane was stirred and refluxed overnight. The warm solution was saturated with water and allowed to cool. The solution was poured onto water and extracted with trichloromethane. The extract was washed with water, dried, filtered and evaporated. The residue was purified by filtration over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The filtrate was evaporated and the residue was crystalized from methylbenzene, yielding 3.7 parts (73%) of 3-[4-[4-(4-methoxyphenyl)-1-piperazinyl]phenyl]-1-(1-methylethyl)-2,4-imidazolidinedione; mp. 193.7° C. (38).

Workup

  1. temperaturerefluxed overnight
  2. temperatureto cool
  3. additionThe solution was poured onto water
  4. extractionextracted with trichloromethane
  5. washThe extract was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. filtrationThe residue was purified by filtration over silica gel using
  10. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  11. customThe filtrate was evaporated
  12. customthe residue was crystalized from methylbenzene

Sources & evidence

ORD record
ord-1df4510d18a141489dbf74c46ad49f0f
Source dataset
uspto-grants-1989_08
Patent number
US04861879

Reaction notes

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