p-Toluenesulfonic acid → HCID 57094954, compound

HRID 864501Notes

Reaction equation

HRID 864501 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) δ 7.7 (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-d97e6dacc3f846b2b33a72cacd8bd6a5
Source dataset
uspto-grants-1996_10
Patent number
US05563158

Reaction notes

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