Formaldehyde → HCID 13037606, compound

HRID 1074398Notes

Reaction equation

HRID 1074398 reaction equation
[C:1]([CH2:3][C:4](O)=O)#[N:2].[NH:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][OH:14])[CH2:8]1.[CH2:15]=O>O1CCOCC1>[OH:14][CH2:13][CH:9]1[CH2:10][CH2:11][CH2:12][N:7]([CH2:15][C:3](=[CH2:4])[C:1]#[N:2])[CH2:8]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 9740Cyanoacetic acidHCID 107308Piperidin-3-ylmethanol

Product 1

HCID 13037606HCID 13037606, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Cyanoacetic acid (25.5 g., 0.3 mole) was dissolved in 75 ml. of dioxane, cooled to 0°-10° C., and with the cooling bath in place, 3-piperidinemethanol (34.5 g., 0.3 mole) dripped in. The temperature then rose upon the addition of 37% aqueous formaldehyde (50 g., 0.6 mole) to 30° C. with the cold bath removed. After mixing overnight at room temperature, the mixture was concentrated in a rotary evaporator, saturated with sodium chloride and extracted with ether. The organic phase was washed with sodium carbonate solution, dried and concentrated. The residue yielded 43.8 g.; 38 g. was fractionally distilled and the product isolated, 22.4 g., b.p. 137° C./0.4 mm.

Workup

  1. customremoved
  2. additionAfter mixing overnight at room temperature
  3. concentrationthe mixture was concentrated in a rotary evaporator, saturated with sodium chloride
  4. extractionextracted with ether
  5. washThe organic phase was washed with sodium carbonate solution
  6. customdried
  7. concentrationconcentrated
  8. customThe residue yielded 43.8 g
  9. distillationwas fractionally distilled
  10. customthe product isolated

Sources & evidence

ORD record
ord-9b17be0d209a415e9cfabfe91b01f617
Source dataset
uspto-grants-1983_07
Patent number
US04391812

Reaction notes

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