Butanal → 1-Butyl-4-(4-methoxyphenyl)piperazine dihydrochloride

HRID 2198522

Reaction equation

HRID 2198522 reaction equation
[ClH:1].Cl.[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.[CH:17](=O)[CH2:18][CH2:19][CH3:20].C([O-])(=O)C.[Na+].[H][H]>[Pd].CO>[ClH:1].[ClH:1].[CH2:17]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH3:3])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)[CH2:18][CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 261ButanalHCID 517045Sodium AcetateHCID 27237001-(4-Methoxyphenyl)-piperazine, dihydrochlorideHCID 178418361HCID 178418361, compound

Product 1

HCID 205193341-Butyl-4-(4-methoxyphenyl)piperazine dihydrochlorideYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 13.2 parts of 1-(4-methoxyphenyl)piperazine dihydrochloride, 5.1 parts of 1-butanal, 9 parts of sodium acetate and 80 parts of methanol is hydrogenated at normal pressure and at room temperature with 1 part of palladium-on-charcoal catalyst. After the calculated amount of hydrogen is taken up, the catalyst is filtered off and the filtrate is evaporated. Water is added to the residue and the product is precipitated. It is filtered off, washed with water and converted into the hydrochloride salt in ethanol and 2-propanol. Upon the addition of 2,2'-oxybispropane, the salt is precipitated. It is filtered off and crystallized from a mixture of ethanol and 2,2'-oxybispropane, yielding 13.1 parts (81%) of 1-butyl-4-(4-methoxyphenyl)piperazine dihydrochloride; mp. 214.2° C.

Workup

  1. filtrationthe catalyst is filtered off
  2. customthe filtrate is evaporated
  3. additionWater is added to the residue
  4. customthe product is precipitated
  5. filtrationIt is filtered off
  6. washwashed with water
  7. additionUpon the addition of 2,2'-oxybispropane
  8. customthe salt is precipitated
  9. filtrationIt is filtered off
  10. customcrystallized from a mixture of ethanol and 2,2'-oxybispropane

Sources & evidence

ORD record
ord-67ad504f42b642f882d4afe7fbafc83d
Source dataset
uspto-grants-1982_11
Patent number
US04358449

Linked notes

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