Formic Acid → HCID 14879076, compound

HRID 1199079Notes

Reaction equation

HRID 1199079 reaction equation
[CH2:1]([CH:3]([NH:19][CH3:20])[CH:4]([CH2:17][CH3:18])[C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1)[CH3:2].C=O.[CH:23](O)=O>CN(C=O)C>[CH2:1]([CH:3]([N:19]([CH3:23])[CH3:20])[CH:4]([CH2:17][CH3:18])[C:5]1[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 712FormaldehydeHCID 22163988HCID 22163988, compound

Product 1

HCID 14879076HCID 14879076, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 35.4 g (0.126 mole) of α,β-diethyl-3,4,5-trimethoxy-N-methylbenzeneethanamine, 25.6 g (0.316 mole) formalin, 15 g (0.316 mole) formic acid in 350 ml DMF was heated under reflux for five hours. The mixture was partitioned between water and methylene chloride. The organic layer was dried with MgSO and evaporated in vacuo. The residue was warmed at 0.75 Torr for one hour. There was obtained 34 g (91% yield) of α,β-diethyl-3,4,5-trimethoxy-N,N dimethylbenzeneethanamine as an oil 1H NMR (CHCl3): 6.7 (s, 2H); 3.8 (s 9H); 2.7-2.2 (m, 2H); 2.2 (s, 6H); 2.0-1.2 (m, 4H); 0.9 (t, 3H); 0.7 (t, 3H).

Workup

  1. temperatureunder reflux for five hours
  2. customThe mixture was partitioned between water and methylene chloride
  3. dry with materialThe organic layer was dried with MgSO
  4. customevaporated in vacuo
  5. temperatureThe residue was warmed at 0.75 Torr for one hour

Sources & evidence

ORD record
ord-16703f2c4bf140b484d3080649ae98d7
Source dataset
uspto-grants-1990_02
Patent number
US04898889

Reaction notes

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