Acetic Acid → 4-(Piperidin-1-yl)benzoic acid

HRID 2244281Notes

Reaction equation

HRID 2244281 reaction equation
[N:1]1([C:7]2[CH:14]=[CH:13]C(C#N)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[C:17]([OH:20])(=[O:19])[CH3:18]>Cl>[N:1]1([C:7]2[CH:14]=[CH:13][C:18]([C:17]([OH:20])=[O:19])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 7667714-piperidin-1-ylbenzonitrile

Product 1

HCID 7645994-(Piperidin-1-yl)benzoic acidYield 88%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 4-piperidin-1-ylbenzonitrile of Step A (1.13 g, 6.07 mmol) in acetic acid (30 mL) and concentrated hydrochloric acid (30 mL) was stirred at 100° C. for 18 hours. The cooled reaction mixture was then poured over crushed ice, the pH adjusted to 3 by the addition of 2 M sodium hydroxide, and the resulting suspension allowed to stand overnight. The solid product was filtered and dried at 50° C. in vacuo overnight to afford the title compound (1.09 g, 88%) as a white solid, m.p. 225-230° C. (dec).

Workup

  1. customThe cooled reaction mixture
  2. additionwas then poured
  3. customover crushed ice
  4. waitto stand overnight
  5. filtrationThe solid product was filtered
  6. customdried at 50° C. in vacuo overnight

Sources & evidence

ORD record
ord-69bf6e2ca420445ea1d9fe601db1f11f
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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