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

HRID 2115678Notes

Reaction equation

HRID 2115678 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)nicotinonitrile 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-324b2bc4802548f281f13014666e7f02
Source dataset
uspto-grants-2008_10
Patent number
US07435743B2

Reaction notes

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