Acetic Acid → HCID 21558493, compound

HRID 1578693Notes

Reaction equation

HRID 1578693 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[NH2:19][C:20]1[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:21]=1[N:27]1[CH:31]=[CH:30][CH:29]=[CH:28]1>C(O)C>[ClH:26].[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([NH:19][C:20]3[C:21](=[CH:22][CH:23]=[C:24]([Cl:26])[CH:25]=3)[N:27]3[CH:28]=[CH:29][CH:30]=[C:31]23)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 192201-Benzyl-4-piperidoneHCID 106554015-chloro-2-(1H-pyrrol-1-yl)aniline

Product 1

HCID 21558493HCID 21558493, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.29 g (0.028 mole) of 1-benzyl-4-piperidone and 2 ml. of glacial acetic acid are added to a solution of 5.0 g (0.026 mole) of 1-(2-amino-4-chlorophenyl)pyrrole [Example 13(b)] in 80 ml. of absolute ethanol. The solution is refluxed, leaving a yellow oil. The oil is washed with a potassium hydroxide solution, then water, and placed in a refrigerator overnight. The tan solid which forms is dissolved in ether, and ethereal hydrogen chloride is added. The resulting precipitate is washed with water and dried to give 1'-benzyl-7-chloro-4,5-dihydrospiro[pyrrolo(1,2-a)quinoxaline-4,4'-piperidine]hydrochloride, m.p. 282°-283° C.

Workup

  1. temperatureThe solution is refluxed
  2. customleaving a yellow oil
  3. washThe oil is washed with a potassium hydroxide solution
  4. customplaced in a refrigerator overnight
  5. dissolutionThe tan solid which forms is dissolved in ether
  6. additionethereal hydrogen chloride is added
  7. washThe resulting precipitate is washed with water
  8. customdried

Sources & evidence

ORD record
ord-1634684d88724983a4033613af82b950
Source dataset
uspto-grants-1976_02
Patent number
US03939159

Reaction notes

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