Formaldehyde → HCID 131711378, compound

HRID 66114Notes

Reaction equation

HRID 66114 reaction equation
[CH2:1]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[CH2:3][CH2:2]1.[ClH:13].Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[CH2:29]=O>C(O)C>[ClH:13].[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH:3]2[CH2:2][CH2:1][CH2:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:4]2=[O:5])[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 70003BenzosuberoneHCID 3016017Piperazine, 1-(2-methoxyphenyl)-, hydrochloride (1:2)

Product 1

HCID 131711378HCID 131711378, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of benzosuberone (4.5 g), N-(2-methoxyphenyl)piperazine, dihydrochloride (7.5 g), 37% formalin (2.5 g), and absolute ethanol (30 ml) is heated on a steam bath with stirring for 30 minutes. The solution is allowed to stand overnight at room temperature. The reaction mixture is then concentrated in vacuo, basified with concentrated ammonium hydroxide, and extracted with ether. Concentration of the dried ether solution gives a crude product that is chromatographed on a silica gel column using ethyl acetate. The ethyl acetate solution is concentrated and the residue treated with ethereal hydrogen chloride to provide 3.9 g (32%) of a crystalline solid. Crystallization from acetonitrile/ether gives 2.5 g of pure hydrochloride salt, melting point 164°-166° C.

Workup

  1. temperatureis heated on a steam bath
  2. waitto stand overnight at room temperature
  3. concentrationThe reaction mixture is then concentrated in vacuo
  4. extractionextracted with ether
  5. customConcentration of the dried ether solution gives a crude product that
  6. customis chromatographed on a silica gel column
  7. concentrationThe ethyl acetate solution is concentrated
  8. additionthe residue treated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-c87b3d8835cf4fbfb25390fc4642384a
Source dataset
uspto-grants-1978_12
Patent number
US04130646

Reaction notes

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