Acetic Acid → 5-(3-Piperidinyl)-1-pentanol acetate

HRID 2403834Notes

Reaction equation

HRID 2403834 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][OH:12])[CH:2]=1.[C:13](O)(=[O:15])[CH3:14]>CO.[Pt](=O)=O>[C:13]([O:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][NH:1][CH2:2]1)(=[O:15])[CH3:14]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 107970615-(3-Pyridinyl)-4-pentyn-1-ol

Product 1

HCID 671812975-(3-Piperidinyl)-1-pentanol acetate

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-(3-pyridinyl)-4-pentyn-1-ol (4.99 g, 31.0 mmol) in acetic acid (150 mL) was hydrogenated over platinum (IV) oxide (1.4 g, 6.16 mmol) for 18 hours. The mixture was filtered through a Celite cartridge, washed through with acetic acid and evaporated in vacuo to give a yellow oil. This was loaded in methanol and eluted on an aminopropyl (NH2) cartridge (70 g) with methanol (400 ml). The solvent was evaporated in vacuo to give the title compound as a colourless oil which solidified after being under vacuum for 18 hours (7.4 g).

Workup

  1. filtrationThe mixture was filtered through a Celite cartridge
  2. washwashed through with acetic acid
  3. customevaporated in vacuo
  4. customto give a yellow oil
  5. washeluted on an aminopropyl (NH2) cartridge (70 g) with methanol (400 ml)
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-41bf1812ed1649adbc78462eab38e06a
Source dataset
uspto-grants-2014_08
Patent number
US08802684B2

Reaction notes

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