Water → HCID 20528722, compound

HRID 67172

Reaction equation

HRID 67172 reaction equation
[O:1]=[C:2]([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1.[BH4-].[Na+].C(OCC)(=O)C.O>CO>[OH:1][CH:2]([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][N:7]=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 805524-PyridinylacetoneHCID 4311764Sodium borohydride

Product 1

HCID 20528722HCID 20528722, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 4-(2'-oxopropyl)-pyridine (13.7 g) in methanol (135 ml), sodium borohydride (3.0 g) was added in portions. After stirring for 2 hours, the mixture was taken to dryness in vacuo. The residue was distributed between ethyl acetate and a minimum of water sufficient to dissolve inorganic salts. The organic phase was dried and evaporated to yield 4-(2'-hydroxypropyl)-pyridine as a colourless oil. The oil was dissolved in acetic acid (100 ml) and hydrogenated in the presence of Adam's catalyst (1 g) until 3 equivalents of hydrogen were consumed. The catalyst was removed by filtration and the filtrate was concentrated in vacuo to yield crude 4-(2'-hydroxypropyl)-piperidine which was used directly in the next step. In analogous manner 4-(2'-hydroxybutyl)-piperidine was prepared from 4-(2'-oxobutyl)-pyridine.

Workup

  1. customThe organic phase was dried
  2. customevaporated

Sources & evidence

ORD record
ord-0a3ca95f42354c27b723903cffaa7c8a
Source dataset
uspto-grants-1982_08
Patent number
US04345071

Linked notes

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