Hydrochloric Acid → 2-Amino-6-(2-hydroxyphenyl)-4-(3-piperidinyl)nicotinonitrile hydrochloride

HRID 1767341Notes

Reaction equation

HRID 1767341 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]2)[CH:5]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[N:3]=1.[ClH:30]>O1CCOCC1>[ClH:30].[NH2:1][C:2]1[N:3]=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[OH:29])[CH:5]=[C:6]([CH:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)[C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135550611Tert-butyl 3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-1-piperidinecarboxylate

Product 1

HCID 1355506262-Amino-6-(2-hydroxyphenyl)-4-(3-piperidinyl)nicotinonitrile hydrochlorideYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of tert-butyl 3-[2-amino-3-cyano-6-(2-hydroxyphenyl)-4-pyridinyl]-1-piperidinecarboxylate (0.170 g, 0.431 mmol) in dioxane (30 mL) was added 4N HCl in dioxane (3 mL). The mixture was stirred at room temperature for 12 hrs. The resulting precipitates were collected by filtration and the filtrate was washed with dioxane to give 2-amino-6-(2-hydroxyphenyl)-4-(3-piperidinyl)nicotino-nitrile hydrochloride(0.075 g, yield; 53%).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washthe filtrate was washed with dioxane

Sources & evidence

ORD record
ord-0869c3c7c9a54f6f9574014ff32383a6
Source dataset
uspto-grants-2007_06
Patent number
US07232909B2

Reaction notes

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