Isobutyraldehyde → Morpholine, 4-(2-methyl-1-propenyl)-

HRID 2378039Notes

Reaction equation

HRID 2378039 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH:7](=O)[CH:8]([CH3:10])[CH3:9]>>[O:4]1[CH2:5][CH2:6][N:1]([CH:7]=[C:8]([CH3:10])[CH3:9])[CH2:2][CH2:3]1

Participants

3

Reactant 2

HCID 6561IsobutyraldehydeHCID 8083Morpholine

Product 1

HCID 102255Morpholine, 4-(2-methyl-1-propenyl)-

Procedure

Morpholine (21.78 g, 0.25 mol) and isobutyraldehyde (18.02 g, 0.25 mol) were heated to reflux as a neat mixture, in a 100 ml round bottom flask with a Dean Stark Trap attached. After the mixture was refluxed overnight, the reaction mixture was purified by vacuum distillation. The pure enamine product (15.01 g, 0.10 mol, 42%) had a 1H-NMR (CDCl3): 5.32 (s, 1H), 3.72 (t, 4H), 2.87 (t, 4H), 1.81 (s, 3H), 1.68 (s, 3H) It had LC-MS (ES+): 142 [MH]+ m/e.

Workup

  1. temperatureto reflux as a neat mixture, in a 100 ml round bottom flask with a Dean Stark Trap
  2. temperatureAfter the mixture was refluxed overnight
  3. distillationthe reaction mixture was purified by vacuum distillation

Sources & evidence

ORD record
ord-6b4e393c562c467988fe4ba8a094f71d
Source dataset
uspto-grants-2008_12
Patent number
US07470722B2

Reaction notes

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