6-(4-Pyridinyl)-5-hexyn-1-ol → 6-(4-Pyridinyl)-5-hexyn-1-ol

HRID 1044933Notes

Reaction equation

HRID 1044933 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:3][CH:2]=1>C(O)(=O)C.CO>[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])[CH2:3][CH2:2]1.[N:1]1[CH:6]=[CH:5][C:4]([C:7]#[C:8][CH2:9][CH2:10][CH2:11][CH2:12][OH:13])=[CH:3][CH:2]=1

Participants

5

Reactant 1

HCID 583060816-(4-Pyridinyl)-5-hexyn-1-ol

Product 2

HCID 27846296-(4-Piperidinyl)-1-hexanolHCID 583060816-(4-Pyridinyl)-5-hexyn-1-olYield 249.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 887MethanolSolvent

Procedure

A solution of 6-(4-pyridinyl)-5-hexyn-1-ol (2.36 g, 13.47 mmol) in acetic acid (25 ml) was hydrogenated over platinium (IV) oxide (0.612 g, 2.69 mmol) for 72 hours. The mixture was filtered through a Celite cartridge, washed through with acetic acid and then ethyl acetate. The combined filtrate and washings were evaporated in vacuo to give a dark brown oil. The mixture was hydrogenated again as before, this time in 100 ml acetic acid for 20 hours. The mixture was filtered through a Celite cartridge, washed through with acetic acid and then ethyl acetate. The combined filtrate and washings were evaporated in vacuo to give a dark brown oil. The sample was loaded in methanol and eluted on aminopropyl (NH2) 70 g using MeOH. The solvent evaporated in vacuo to give the title compound contaminated with 10% 6-(4-pyridinyl)-5-hexyn-1-ol as a dark brown gum (2.94 g).

Workup

  1. filtrationThe mixture was filtered through a Celite cartridge
  2. washwashed through with acetic acid
  3. customThe combined filtrate and washings were evaporated in vacuo
  4. customto give a dark brown oil
  5. customfor 20 hours
  6. filtrationThe mixture was filtered through a Celite cartridge
  7. washwashed through with acetic acid
  8. customThe combined filtrate and washings were evaporated in vacuo
  9. customto give a dark brown oil
  10. washeluted on aminopropyl (NH2) 70 g
  11. customThe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-66a625f34e9a48e19957b6806ee2484d
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

Loading…