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

HRID 1044895Notes

Reaction equation

HRID 1044895 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>[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

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 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 platinium (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-f09c16ccc88b491580a933a8e388fb76
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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