Water → N-butylpiperidine-4-carboxamide

HRID 1389152Notes

Reaction equation

HRID 1389152 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH2:10]([NH2:14])[CH2:11][CH2:12][CH3:13].O>C1(C)C=CC=CC=1>[CH2:10]([NH:14][C:1]([CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1)=[O:8])[CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 962WaterHCID 8007ButylamineHCID 417436Pyridine-4-carbonyl chloride

Product 1

HCID 16228130N-butylpiperidine-4-carboxamideYield 14.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Isonicotinoyl chloride (100.0 g) was added over 1 hour to a solution of n-butylamine (51.6 g) in toluene (600 ml) at 0°. The mixture was allowed to stand overnight, heated on a steam bath for 1/2 hour, then water was added. The aqueous layer was separated, basified to about pH 12 (NaOH), and extracted with ethyl acetate (2 times). The combined organic extracts were dried (MgSO4), evaporated and the resulting residue (36.0 g) dissolved in acetic acid (400 ml) and hydrogenated at 50 p.s.i./30° in the presence of platinum oxide. The catalyst was removed by filtration, the solution evaporated to dryness, the residue basified to about pH 12 (Na2CO3), and extracted with chloroform. The chloroform extracts were dried (Na2SO4) and evaporated to give 4-(N-n-butylcarbamoyl)piperidine, (18.7 g), m.p. 75°-79°. The oxalate salt was prepared in isopropanol from the free base and oxalic acid and was recrystallised from isopropanol/ethyl acetate, m.p. 143°-144° .

Workup

  1. temperatureheated on a steam bath for 1/2 hour
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2 times)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customevaporated
  6. dissolutionthe resulting residue (36.0 g) dissolved in acetic acid (400 ml)
  7. custom30°
  8. customThe catalyst was removed by filtration
  9. customthe solution evaporated to dryness
  10. extractionextracted with chloroform
  11. dry with materialThe chloroform extracts were dried (Na2SO4)
  12. customevaporated

Sources & evidence

ORD record
ord-6e3b5492415c4f40a636e8e10bb80619
Source dataset
uspto-grants-1981_01
Patent number
US04243666

Reaction notes

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