Sodium → 4-(Piperidin-4-yl)benzoic acid

HRID 1264317Notes

Reaction equation

HRID 1264317 reaction equation
[Na].[N:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](C(O)=O)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C[C:18]([OH:20])=[O:19].CO>O=[Pt]=O>[NH:2]1[CH2:3][CH2:4][CH:5]([C:8]2[CH:9]=[CH:10][C:11]([C:18]([OH:20])=[O:19])=[CH:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10129899Acetic acid methanolHCID 121307752-(Pyridin-4-yl)benzoic acid

Product 1

HCID 180024624-(Piperidin-4-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 345198Adams' catalystCatalyst

Procedure

To the sodium salt of 4-pyridine benzoic acid (500 mg, 2.25 mmol) suspended in 20% AcOH/MeOH (20 ml) was added PtO2 (250 mg) and the mixture was hydrogenated at 50 psi with agitation (Parr) for 4 h. The solution was filtered through celite, washed with MeOH (3×5 ml), evaporated with hexane (4×) to azeotrope the acetic acid. TLC of the crude (EtOH/H2O/NH4OH 10:1:1) shows no starting material, but did show 2 more polar spots. After evaporation from hexane, the white solid (596 mg crude, still with residual HOAc) was dried in a vacuum overnight, and used without further purification in subsequent steps. MS m/z [M+H]+.

Workup

  1. filtrationThe solution was filtered through celite
  2. washwashed with MeOH (3×5 ml)
  3. customevaporated with hexane (4×)
  4. customAfter evaporation from hexane
  5. dry with materialthe white solid (596 mg crude, still with residual HOAc) was dried in a vacuum overnight
  6. customused without further purification in subsequent steps

Sources & evidence

ORD record
ord-40895aceb72d4356bd33d07f005f3797
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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