Sodium Hydroxide → N-((2-aminophenyl)methyl)-1-benzylpiperidin-4-amine

HRID 2166896Notes

Reaction equation

HRID 2166896 reaction equation
Cl.Cl.Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][CH:14]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[OH-].[Na+]>O>[CH2:4]([N:11]1[CH2:12][CH2:13][CH:14]([NH:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[NH2:25])[CH2:15][CH2:16]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 204971641-Benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochloride

Product 1

HCID 13051020N-((2-aminophenyl)methyl)-1-benzylpiperidin-4-amineYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In this reference example, 1.10 g of 1-benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine trihydrochloride is mixed with 5 ml of water. Then, 15 ml of 1 N aqueous sodium hydroxide is added to the solution with cooling. The mixture is extracted with 20 ml of chloroform four times. The chloroform layer is washed with 20 ml of water two times. The resultant layer is dried and concentrated under reduced pressure to obtain 670 mg of 1-benzyl-4-[N-(o-aminobenzyl)-amino]-piperidine as an oily residue.

Workup

  1. temperaturewith cooling
  2. extractionThe mixture is extracted with 20 ml of chloroform four times
  3. washThe chloroform layer is washed with 20 ml of water two times
  4. dry with materialThe resultant layer is dried
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-90d43fd326a54c4e8463836932163bb9
Source dataset
uspto-grants-1983_06
Patent number
US04390536

Reaction notes

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