Hydrochloric Acid → 5-[({4-[2-(3-Cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinic acid

HRID 2074337Notes

Reaction equation

HRID 2074337 reaction equation
[OH-].[Na+].C1COCC1.[C:8]([C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]3[CH:28]=[N:29][CH:30]=[C:31]([CH:36]=3)[C:32]([O:34]C)=[O:33])=[O:25])[CH2:20][CH2:19]2)[CH:13]=[CH:14][CH:15]=1)#[N:9].Cl>O>[C:8]([C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]3[CH:28]=[N:29][CH:30]=[C:31]([CH:36]=3)[C:32]([OH:34])=[O:33])=[O:25])[CH2:20][CH2:19]2)[CH:13]=[CH:14][CH:15]=1)#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 57507814Methyl 5-[({4-[2-(3-cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinate

Product 1

HCID 575078155-[({4-[2-(3-Cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinic acidYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An aqueous 1 M sodium hydroxide solution (0.69 ml) was added to a THF (5 ml)/water (4 ml) solution of methyl 5-[({4-[2-(3-cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinate (272 mg), followed by stirring overnight at room temperature. 1 M hydrochloric acid (0.69 ml) was added to the reaction liquid, and the crystal precipitated was collected by filtration. The crystal was washed with a hot methanol/water solution, and dried to obtain 5-[({4-[2-(3-cyanophenyl)ethyl]-1-piperidyl}carbonyl)oxy]nicotinic acid (240 mg).

Workup

  1. customthe crystal precipitated
  2. filtrationwas collected by filtration
  3. washThe crystal was washed with a hot methanol/water solution
  4. customdried

Sources & evidence

ORD record
ord-7cc43f3ba2fa475786e665e6c8e86db8
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

Loading…