Acetic Acid → HCID 20569927, compound

HRID 1577850Notes

Reaction equation

HRID 1577850 reaction equation
[ClH:1].[OH:2][CH:3]([CH3:11])[CH2:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1.[H][H].[C:14](O)(=[O:16])[CH3:15]>[Pt]=O>[ClH:1].[C:14]([O:2][CH:3]([CH3:11])[CH2:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 20569937HCID 20569937, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20569927HCID 20569927, compound

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst

Procedure

4-(2-Hydroxypropyl)pyridine hydrochloride (11 g) in glacial acetic acid (110 ml) was hydrogenated at 50°/50 p.s.i. over a platinum oxide catalyst until uptake of hydrogen ceased. The catalyst was removed by filtration and the filtrate was evaporated to dryness in vacuo. The residue was triturated with ether (100 ml) and the resultant solid was recrystallized from ethyl acetate-isopropyl alcohol (1:1) to give 4-(2-acetoxypropyl)piperidine hydrochloride (1 g) m.p. 188°-191°.

Workup

  1. customwas hydrogenated at 50°
  2. customThe catalyst was removed by filtration
  3. customthe filtrate was evaporated to dryness in vacuo
  4. customThe residue was triturated with ether (100 ml)
  5. customthe resultant solid was recrystallized from ethyl acetate-isopropyl alcohol (1:1)

Sources & evidence

ORD record
ord-2486ec8f0ba34b5cac40168e07ce130b
Source dataset
uspto-grants-1981_09
Patent number
US04289772

Reaction notes

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