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

HRID 412253Notes

Reaction equation

HRID 412253 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-b12f330fcc7a4a3f90f8545f65adbfa3
Source dataset
uspto-grants-2003_05
Patent number
US06562811B1

Reaction notes

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