Hydrochloric Acid → HCID 19972637, compound

HRID 1452317Notes

Reaction equation

HRID 1452317 reaction equation
[CH2:1]=O.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.[ClH:17].[C:18]([C:21]1[C:30]2[O:29][C:28]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[C:27]([CH3:37])[C:26](=[O:38])[C:25]=2[CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH3:19]>CO.C(OCC)C.O1CCOCC1>[ClH:17].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:1][CH2:19][C:18]([C:21]2[C:30]3[O:29][C:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:27]([CH3:37])[C:26](=[O:38])[C:25]=3[CH:24]=[CH:23][CH:22]=2)=[O:20])[CH2:13][CH2:12]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 13461-(2-Methoxyphenyl)piperazineHCID 22994586HCID 22994586, compound

Product 1

HCID 19972637HCID 19972637, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent4×HCID 3283Diethyl EtherSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 10 ml of 37% formaldehyde in 15 ml of methanol was dropped, over a period of 3 minutes at 0° C., into a solution of 5.75 g of 1-(2-methoxyphenyl)piperazine in 10 ml of methanol. After 12 hours at 0° C., the mixture was stripped in vacuo and redissolved in 15 ml of methanol. 20 ml of 3.6N hydrogen chloride in diethyl ether was added at 0° C. After stripping in vacuo, the residue was suspended in 15 ml of 1,4-dioxane. A solution of 8.3 g of Intermediate V in 100 ml of 1,4-dioxane was added under stirring at 20°-25° C. After stirring for 8 hours at reflux the reaction mixture was cooled to 30°-40° C. 50 ml of methanol was added and the mixture was refluxed for a further 2 hours. After cooling to 20°-25° C., the resultant solution was diluted with 300 ml of diethyl ether. Stirring was continued for a further 3 hours at the same temperature. The title compound was collected by suction filtration and recrystallization from ethanol. Yield 4 g, m.p. 209°-210° C.

Workup

  1. stirringAfter stirring for 8 hours
  2. temperatureat reflux the reaction mixture
  3. temperaturewas cooled to 30°-40° C
  4. temperaturethe mixture was refluxed for a further 2 hours
  5. temperatureAfter cooling to 20°-25° C.
  6. stirringStirring
  7. waitwas continued for a further 3 hours at the same temperature
  8. filtrationThe title compound was collected by suction filtration and recrystallization from ethanol

Sources & evidence

ORD record
ord-7366d85593564afa9f6cc74db362fb52
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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