Morpholine → Trimetozine

HRID 1836799Notes

Reaction equation

HRID 1836799 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[C:12](Cl)=[O:13]>C1(C)C=CC=CC=1>[CH3:21][O:20][C:16]1[CH:15]=[C:11]([CH:10]=[C:9]([O:8][CH3:7])[C:17]=1[O:18][CH3:19])[C:12]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)=[O:13]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-

Product 1

HCID 12478TrimetozineYield 86%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Morpholine (0.8 mL) was slowly added to a solution composed of toluene (10 mL) and 3,4,5-trimethoxybenzoyl chloride (1.1 g). The reaction was accompanied by evolution of heat and precipitation of morpholine hydrochloride. After 3 hours, the solution was filtered and concentrated in vacuo to afford a white solid which was recrystallized from ethanol to afford colorless needles (1.2 g, 86%): m.p. 119.8-120.7° C., lit3c m.p. 120-121° C.; EIMS m/z 281 (M+), 266, 195; 1H NMR δ 6.63 (2H, s, H2,6), 3.87 (6H, s, OCH3×2), 3.86 (3H, s, OCH3), 3.70 (8H, bs, CH2×4).

Workup

  1. temperatureof heat
  2. customprecipitation of morpholine hydrochloride
  3. filtrationthe solution was filtered
  4. concentrationconcentrated in vacuo
  5. customto afford a white solid which
  6. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-19897944c2844681afaa0a6cccd79f73
Source dataset
uspto-grants-2004_08
Patent number
US06777578B2

Reaction notes

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