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

HRID 444839Notes

Reaction equation

HRID 444839 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 37A) were dissolved in 40 ml of a solution of hydrochloric acid in dioxane (4 M), and the mixture was stirred at RT for 2 h. After the reaction had gone to completion the solvent was concentrated to half of its original volume and 20 ml of diethyl ether were added. The precipitate was filtered off and dried. This gave 1.80 g (100% of theory) of the product as a solid.

Workup

  1. concentrationwas concentrated to half of its original volume and 20 ml of diethyl ether
  2. additionwere added
  3. filtrationThe precipitate was filtered off
  4. customdried

Sources & evidence

ORD record
ord-5b21e6b7b52545c1bd9c4c61f482b877
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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