Hydrochloric Acid → 4-Methyl-N-[(3R)-3-piperidyl]pyridin-2-amine dihydrochloride

HRID 1775339Notes

Reaction equation

HRID 1775339 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:3]=1.[ClH:22]>CO>[ClH:22].[ClH:22].[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C@@H:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 26385049(R)-tert-butyl 3-((4-methylpyridin-2-yl)amino)piperidine-1-carboxylate

Product 1

HCID 898259614-Methyl-N-[(3R)-3-piperidyl]pyridin-2-amine dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

tert-Butyl (3R)-3-[(4-methyl-2-pyridyl)amino]piperidine-1-carboxylate (271 mg, 0.93 mmol) was dissolved in methanol (1 ml). Hydrochloric acid (4N in dioxane, 4.65 ml, 18.6 mmol) was added and the mixture was stirred at room temperature for three hours. The mixture was concentrated under reduced pressure, the residue was treated twice with diethylether and separated by decantation, dissolved in methanol and evaporated to dryness to yield 246 mg (quantitative) MS (ESI) m/z=192.2 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was treated twice with diethylether
  3. customseparated by decantation
  4. dissolutiondissolved in methanol
  5. customevaporated to dryness
  6. customto yield 246 mg (quantitative)

Sources & evidence

ORD record
ord-d8ea6355af4246b08cb719400790efda
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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