Hydrochloric Acid → HCID 11530471, compound

HRID 2074331Notes

Reaction equation

HRID 2074331 reaction equation
[C:1]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH:27]=3)[C:23]([O:25]C)=[O:24])=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].Cl>C1COCC1.CO>[C:1]1([CH2:7][CH2:8][CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]3[CH:19]=[N:20][CH:21]=[C:22]([CH:27]=3)[C:23]([OH:25])=[O:24])=[O:16])[CH2:13][CH2:14]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 57421843HCID 57421843, compound

Product 1

HCID 11530471HCID 11530471, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 5-({[4-(2-phenylethyl)piperidin-1-yl]carbonyl}oxy)nicotinate (3.95 g) was dissolved in THF (32 ml) and methanol (16 ml), and under ice cooling, aqueous 1 M sodium hydroxide solution (16 ml) was dropwise added thereto. This was stirred at room temperature for 30 minutes, and under ice cooling, this was neutralized with 1 M hydrochloric acid (16 ml). The colorless solid precipitated was collected by filtration, and recrystallized from methanol/water to obtain 5-({[4-(2-phenylethyl)piperidin-1-yl]carbonyl}oxy)nicotinic acid (3.70 g).

Workup

  1. customThe colorless solid precipitated
  2. filtrationwas collected by filtration
  3. customrecrystallized from methanol/water

Sources & evidence

ORD record
ord-ad7ace04c2ba4f83ae4cdb5e42f959d0
Source dataset
uspto-grants-2011_04
Patent number
US07919495B2

Reaction notes

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