1-Butyl-4-piperidone → HCID 20263893, compound

HRID 464046Notes

Reaction equation

HRID 464046 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].[NH2:12][N:13]1[CH:17]=[CH:16][CH:15]=[CH:14]1.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:5]1[CH2:10][CH2:9][CH:8]([NH:12][N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 899951-Butyl-4-piperidoneHCID 1365891-AminopyrroleHCID 4311764Sodium borohydride

Product 1

HCID 20263893HCID 20263893, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 1-butyl-4-piperidone (6.2 g, 40 mmole) and 1-aminopyrrole (3.3 g, 40 mmole) in 100 ml of toluene was stirred at reflux overnight (about 16 hours). The mixture was cooled and then evaporated to an oil, which in turn was dissolved in 75 ml of isopropanol, and 22 ml of ethanol. To the solution was added NaBH4 (3.8 g, 100 mole). The mixture was stirred at 70° C. for 2 hours and then evaporated, stirred with water and extracted with ethyl acetate-ether. The organic extract was washed with water and saturated NaCl solution, dried (anhydrous MgSO4), filtered and evaporated to 13 g of an oil. This oil was purified by high pressure liquid chromatography (silica, 1% diethylamine/ethyl acetate) to give 8.2 g of an oil of 1-(n-butyl)-4-(1H-pyrrol-1-yl)aminopiperidine.

Workup

  1. temperatureat reflux overnight (about 16 hours)
  2. temperatureThe mixture was cooled
  3. customevaporated to an oil, which in turn
  4. dissolutionwas dissolved in 75 ml of isopropanol
  5. customevaporated
  6. stirringstirred with water
  7. extractionextracted with ethyl acetate-ether
  8. extractionThe organic extract
  9. washwas washed with water and saturated NaCl solution
  10. dry with materialdried (anhydrous MgSO4)
  11. filtrationfiltered
  12. customevaporated to 13 g of an oil
  13. customThis oil was purified by high pressure liquid chromatography (silica, 1% diethylamine/ethyl acetate)

Sources & evidence

ORD record
ord-a039b33bc27f4a0da57e5eaeeb516d3d
Source dataset
uspto-grants-1985_10
Patent number
US04546105

Reaction notes

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