Formamide → N-(4-Hydroxy-1-methyl-4-piperidinylmethyl)formamide

HRID 1253000Notes

Reaction equation

HRID 1253000 reaction equation
[NH2:1][CH2:2][C:3]1([OH:10])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.[CH:11](N)=[O:12]>>[OH:10][C:3]1([CH2:2][NH:1][CH:11]=[O:12])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1

Participants

3

Reactant 2

HCID 713FormamideHCID 64842624-(Aminomethyl)-1-methylpiperidin-4-ol

Product 1

HCID 14153813N-(4-Hydroxy-1-methyl-4-piperidinylmethyl)formamideYield 7%

Conditions

Temperature
145 °C

Procedure

A mixture of 50 g (0.35 mole) of 4(aminomethyl)-1-methyl-4-piperidinol and 15.8 g (0.35 mole) of formamide was stirred at 145° C. for 6 hr and allowed to stand overnight. The mass spectra indicated the starting amine was still present. The reaction mixture was reheated to 160° C. and stirred for 1 hr. The heat was removed and 150 ml of toluene was added. On cooling 61 g of crystals were formed, m.p. 116°-122° C. A 5 g sample was recrystallized from toluene to give 4.2 g of the title compound, m.p. 122°-124° C.

Workup

  1. waitto stand overnight
  2. customwas reheated to 160° C.
  3. stirringstirred for 1 hr
  4. customThe heat was removed
  5. addition150 ml of toluene was added
  6. temperatureOn cooling 61 g of crystals
  7. customwere formed
  8. customA 5 g sample was recrystallized from toluene

Sources & evidence

ORD record
ord-a56f1ff6654d4aebafd5e84cd0711898
Source dataset
uspto-grants-1988_05
Patent number
US04746655

Reaction notes

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