1-Benzyl-4-[N-(o-nitrobenzyl)-amino]-piperidine dihydrochloride → 1-Benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochloride

HRID 2166895Notes

Reaction equation

HRID 2166895 reaction equation
[ClH:1].Cl.[CH2:3]([N:10]1[CH2:15][CH2:14][CH:13]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>[Pd].O>[ClH:1].[ClH:1].[ClH:1].[CH2:3]([N:10]1[CH2:11][CH2:12][CH:13]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])[CH2:14][CH2:15]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 130510191-Benzyl-4-[N-(o-nitrobenzyl)-amino]-piperidine dihydrochloride

Product 1

HCID 204971641-Benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochlorideYield 139.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

In this reference example, 31.8 g of 1-benzyl-4-[N-(o-nitrobenzyl)-amino]-piperidine dihydrochloride, 3.2 g of 10% Pd-C and 500 ml of water are mixed and stirred at room temperature. Then, about 6 l of hydrogen gas is absorbed by the mixture. Then the reaction is discontinued and the Pd-C is removed by filtration. The aqueous solution is adjusted to pH 11 with an aqueous sodium hydroxide and then extracted with ethyl acetate. The organic layer is washed with water, dried and concentrated. The resulting oily product is dissolved in 140 ml of ethanol. Then, 70 ml of a solution of 5.7 N hydrochloric acid in ethyl acetate is added thereto. The white crystals deposited are separated by filtration, washed with ethyl acetate and dried to obtain 23.5 g of a crude product. The crude product is recrystallized from a mixed solvent of methanol and ethyl acetate to obtain 15.0 g of the desired product.

Workup

  1. customThen, about 6 l of hydrogen gas is absorbed by the mixture
  2. customthe Pd-C is removed by filtration
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe resulting oily product is dissolved in 140 ml of ethanol
  8. additionThen, 70 ml of a solution of 5.7 N hydrochloric acid in ethyl acetate is added
  9. customThe white crystals deposited are separated by filtration
  10. washwashed with ethyl acetate
  11. customdried
  12. customto obtain 23.5 g of a crude product
  13. customThe crude product is recrystallized from a mixed solvent of methanol and ethyl acetate

Sources & evidence

ORD record
ord-eaae720783d04478a2c0781bfd37724b
Source dataset
uspto-grants-1983_06
Patent number
US04390536

Reaction notes

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