Hydrochloric Acid → 4-Cbz-aminopiperidine

HRID 445988Notes

Reaction equation

HRID 445988 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]1[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[OH-].[Na+]>CO>[NH:15]1[CH2:14][CH2:13][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 15143051-Boc-4-Cbz-amino-piperidine

Product 1

HCID 15143044-Cbz-aminopiperidineYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate obtained in Example 1a (13.1 g, 39.2 mmol), a 5 N aqueous hydrochloric acid solution (40 ml, 200 mmol) and methanol (40 ml) was stirred at mom temperature for 23 hours. A 5 N aqueous sodium hydroxide solution (40 ml) was added to the reaction mixture under ice-cooling. Water and the solvent were distilled off from the reaction mixture while the mixture was azeotropically distilled with ethanol. Ethanol was added to the residue, the insoluble matter was removed by filtration, and the filtrate was concentrated to give the title compound (9.10 g, yield 99.1%).

Workup

  1. temperaturecooling
  2. distillationWater and the solvent were distilled off from the reaction mixture while the mixture
  3. distillationwas azeotropically distilled with ethanol
  4. additionEthanol was added to the residue
  5. customthe insoluble matter was removed by filtration
  6. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-d8a9c155dc574bdb9a6e6b801bbdf0b2
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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