HCID 626094, compound → Methyl 3,5-diamino-4-(piperidin-1-yl)benzoate

HRID 441317Notes

Reaction equation

HRID 441317 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([N+:20]([O-])=O)[C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([O:9][CH3:10])=[O:8])([O-])=O>[Pd].CO>[NH2:1][C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([NH2:20])[C:13]=1[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 1

HCID 626094HCID 626094, compound

Product 1

HCID 20290383Methyl 3,5-diamino-4-(piperidin-1-yl)benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

15.45 G. of methyl 3,5-dinitro-4-piperidinobenzoate [Rec. trav. chim. 73, 68 (1954)]dissolved in 200 ml. of methanol were hydrogenated under normal pressure and at room temperature in the presence of 1 g. of palladium/carbon (5%). After uptake of the theoretical amount of hydrogen, the solution was filtered off from the catalyst and evaporated. By recrystallization of the residue from ethyl acetate/petroleum ether, there was obtained methyl 3,5-diamino-4-piperidinobenzoate having a melting point 133°-134° C.

Workup

  1. customwere hydrogenated under normal pressure and at room temperature in the presence of 1 g
  2. filtrationAfter uptake of the theoretical amount of hydrogen, the solution was filtered off from the catalyst
  3. customevaporated
  4. customBy recrystallization of the residue from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-7e37b2a1166a44399b36f7b68f5028d7
Source dataset
uspto-grants-1977_08
Patent number
US04039543

Reaction notes

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