Formaldehyde → HCID 3727604, compound

HRID 1957923Notes

Reaction equation

HRID 1957923 reaction equation
[C:1]([NH2:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH2:16]=O>CO>[N:10]1([CH2:16][NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2331BenzamideHCID 8083Morpholine

Product 1

HCID 3727604HCID 3727604, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of benzamide (0.30 g, 2.5 mmol) in MeOH (5 mL) was added morpholine (0.22 g, 2.5 mmol) and the resulting solution was cooled in an ice bath. Formaldehyde (0.215 mL, 2.5 mmol, 37% in water) was then added and the stirred solution was left on ice for 5 min and then it was allowed to stand at RT for another 10 min, and then it was placed in a 70° C. oil bath for 2 h. The solvents were evaporated and the isolated residue (a waxy solid) was chromatographed on a Chromatotron with dichloromethane/methanol mixture, 5:0.2 to 5:0.6 as eluent. The desired fractions were collected and the solvents were evaporated giving Mannich base 18 (0.145 g, 30%) as an oil which solidified in the freezer.

Workup

  1. temperaturethe resulting solution was cooled in an ice bath
  2. waitto stand at RT for another 10 min
  3. customwas placed in a 70° C.
  4. customfor 2 h
  5. customThe solvents were evaporated
  6. customthe isolated residue (a waxy solid) was chromatographed on a Chromatotron with dichloromethane/methanol mixture, 5:0.2 to 5:0.6 as eluent
  7. customThe desired fractions were collected
  8. customthe solvents were evaporated

Sources & evidence

ORD record
ord-08c6d203634846c9bff31000a52de137
Source dataset
uspto-grants-2013_04
Patent number
US08410075B2

Reaction notes

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