Chloroform → 1-(Piperidin-4-yl)propan-1-ol

HRID 1719710Notes

Reaction equation

HRID 1719710 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].C(Cl)(Cl)Cl>C(O)(=O)C.[Pt]=O>[NH:8]1[CH2:9][CH2:10][CH:5]([CH:1]([OH:4])[CH2:2][CH3:3])[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 743431-(4-Pyridinyl)-1-propanone

Product 1

HCID 189186211-(Piperidin-4-yl)propan-1-ol

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 4-propionyl pyridine (10.0 g) in acetic acid (100 cm3) was hydrogenated over platinum oxide (0.5 g) at 60° and 60 p.s.i. pressure for 60 hours. The mixture was filtered through "Avicel" and volatile material was removed in vacuo to give the crude acetate salt (12.0 g). A portion (1 g) was taken into chloroform (20 cm3), washed with 1M sodium hydroxide solution (10 cm3), dried and evaporated to afford 1-(4-piperidyl)propanol, m.p. 50° (0.70 g).

Workup

  1. filtrationThe mixture was filtered through "Avicel" and volatile material
  2. customwas removed in vacuo
  3. customto give the crude acetate salt (12.0 g)
  4. washwashed with 1M sodium hydroxide solution (10 cm3)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-063585d0b8904863809e235a8a4e0a53
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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