1-(2-Methoxyphenyl)piperazine → HCID 131719221, compound

HRID 2259898Notes

Reaction equation

HRID 2259898 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Cl:15][CH2:16][CH2:17][CH2:18][NH:19][C:20]([C:22]1[C:31]2[O:30][C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[C:28]([CH3:38])[C:27](=[O:39])[C:26]=2[CH:25]=[CH:24][CH:23]=1)=[O:21]>>[OH2:2].[ClH:15].[ClH:15].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([C:22]2[C:31]3[O:30][C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:28]([CH3:38])[C:27](=[O:39])[C:26]=3[CH:25]=[CH:24][CH:23]=2)=[O:21])[CH2:11][CH2:10]1.[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:16][CH2:17][CH2:18][NH:19][C:20]([C:22]2[C:31]3[O:30][C:29]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[C:28]([CH3:38])[C:27](=[O:39])[C:26]=3[CH:25]=[CH:24][CH:23]=2)=[O:21])[CH2:11][CH2:10]1.[ClH:15].[ClH:15]

Participants

3

Reactant 2

HCID 13461-(2-Methoxyphenyl)piperazineHCID 15344573HCID 15344573, compound

Product 1

HCID 131719221HCID 131719221, compoundYield 112.3%

Conditions

Temperature
180 °C

Procedure

A mixture of 6.28 g of 1-(2-methoxyphenyl)-piperazine and 5.34 g of Intermediate XXXVII was heated at 180° C. for 5 hours. After cooling, the dark mass was purified by flash chromatography on silica gel, eluting with dichloromethane:methanol (100:3). The fractions containing the title compound were pooled. The solvents were removed in vacuo and the residue was dissolved in boiling ethanol. The solution was filtered, acidified with ethanolic hydrogen chloride, and stood overnight at 20°-25 C. The crude product was collected by filtration and crystallized from ethanol to give 5 g of the title compound, m.p. (177) 182°-186° C.

Workup

  1. temperatureAfter cooling
  2. customthe dark mass was purified by flash chromatography on silica gel
  3. washeluting with dichloromethane:methanol (100:3)
  4. additionThe fractions containing the title compound
  5. customThe solvents were removed in vacuo
  6. dissolutionthe residue was dissolved
  7. filtrationThe solution was filtered
  8. filtrationThe crude product was collected by filtration
  9. customcrystallized from ethanol

Sources & evidence

ORD record
ord-88a179318edc40a7ba28276c4a3b46f6
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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