Hydrochloric Acid → 2-Amino-6-(piperidin-3-ylamino)pyridine-3-carbonitrile hydrochloride

HRID 1182996Notes

Reaction equation

HRID 1182996 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)[CH:5]=[CH:4][C:3]=1[C:22]#[N:23].[ClH:24]>O1CCOCC1>[ClH:24].[NH2:1][C:2]1[C:3]([C:22]#[N:23])=[CH:4][CH:5]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[N:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57911735Tert-butyl 3-[(6-amino-5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate

Product 1

HCID 670603102-Amino-6-(piperidin-3-ylamino)pyridine-3-carbonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2.00 g (6.3 mmol) of tert-butyl 3-[(6-amino-5-cyanopyridin-2-yl)amino]piperidine-1-carboxylate (Example 9A) were dissolved in 40 ml of a hydrochloric acid solution in dioxane (4 M) and stirred at RT for 2 h. On completion of reaction, the solvent was concentrated by half, and 20 ml of diethyl ether were added. The precipitate was filtered off and dried. 1.80 g (100% of theory) of the product were obtained in solid form.

Workup

  1. customOn completion of reaction
  2. concentrationthe solvent was concentrated by half, and 20 ml of diethyl ether
  3. additionwere added
  4. filtrationThe precipitate was filtered off
  5. customdried
  6. custom1.80 g (100% of theory) of the product were obtained in solid form

Sources & evidence

ORD record
ord-665cff7ebd754b8d8e9b01cfab2d583d
Source dataset
uspto-grants-2014_03
Patent number
US08664246B2

Reaction notes

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