Benzaldehyde → 4-Benzylpiperazine-2-carboxamide

HRID 35317Notes

Reaction equation

HRID 35317 reaction equation
S1C=CC=C1.[CH:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH:15]1[C:20]([NH2:22])=[O:21].[H][H]>[Pt].CO.C(O)C>[C:7]1([CH2:6][N:17]2[CH2:18][CH2:19][NH:14][CH:15]([C:20]([NH2:22])=[O:21])[CH2:16]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 8030ThiopheneHCID 3019914Piperazine-2-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 142302664-Benzylpiperazine-2-carboxamideYield 55%

Reagents, catalysts & solvents 3

HCID 23939PlatinumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To 1 part of a solution of 2 parts of thiophene in 40 parts of ethanol were added 2.2 parts of benzaldehyde, 2.6 parts of 2-piperazinecarboxamide and 120 parts of methanol. The whole was hydrogenated at normal pressure and at room temperature with 2 parts of platinum-on-charcoal catalyst 5%. After the calculated amount of hydrogen was taken up, the catalyst was filtered off and the filtrate was evaporated. The solid residue was boiled in 64 parts of acetonitrile. The mixture was filtered and the filtrate was allowed to crystallize at room temperature. The product was filtered off and dried, yielding 2.4 parts (55%) of 4-(phenylmethyl)-2-piperazinecarboxamide; mp. 168.3° C. (intermediate 36).

Workup

  1. filtrationthe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. filtrationThe mixture was filtered
  4. customto crystallize at room temperature
  5. filtrationThe product was filtered off
  6. customdried

Sources & evidence

ORD record
ord-9f193ad997424c4c8d6552e9e1529713
Source dataset
uspto-grants-1988_08
Patent number
US04766125

Reaction notes

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