p-Toluenesulfonic acid → HCID 57094954, compound

HRID 2294792Notes

Reaction equation

HRID 2294792 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][OH:10])=[CH:3][CH:2]=1.[CH3:11][C:12]1[CH:13]=[CH:14][C:15]([S:18](O)(=[O:20])=[O:19])=[CH:16][CH:17]=1>CCO.O=[Pt]=O>[C:12]1([CH3:11])[CH:17]=[CH:16][C:15]([S:18]([O:10][CH2:9][CH2:8][CH2:7][CH:4]2[CH2:5][CH2:6][NH:1][CH2:2][CH2:3]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 729234-Pyridinepropanol

Product 1

HCID 57094954HCID 57094954, compoundYield 112.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

To a solution of 3-(4-pyridyl)propan-1-ol (15.13 g, 0.1103 mol) in EtOH (100 mL) was added p-TsOH (20.98 g, 0.1103 mol) and PtO2 (1.5 g, 6.6 mmol). The resulting mixture was placed on a Parr apparatus and hydrogenated at 55 p.s.i. After 6 hr, the mixture was filtered (EtOH wash) and the filtrate concentrated in vacuo, giving 36.78 g (>100%) of the desired piperidine; 1H NMR (300 MHz, CDCl3) δ7.7 (d, 2H), 7.2 (d, 2H), 3.55 (t, 2H), 3.3 (m, 4H), 2.95 (bt, 2H), 2.38 (s, 3H), 1.95 (bd, 2H), 1.58 (m, 2H), 1.3 (m, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. wash(EtOH wash)
  3. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e8e10892f0ac46f588bc70a13eaeb74c
Source dataset
uspto-grants-1997_11
Patent number
US05691329

Reaction notes

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