Nitrogen → HCID 11367372, compound

HRID 386975Notes

Reaction equation

HRID 386975 reaction equation
N#N.[C:3]1(=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]1=O.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>C1(C)C=CC=CC=1>[N:11]1([C:4]2[C:3](=[O:10])[CH2:8][CH2:7][CH2:6][CH:5]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 947NitrogenHCID 8083MorpholineHCID 130061,2-Cyclohexanedione

Product 1

HCID 11367372HCID 11367372, compoundYield 95.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Synthesis based on literature modified procedure (Ōhashi, M.; Takahashi, T.; Inoue, S.; Sato, K. Bulletin Chemical Society of Japan, 1975; 48:1892). A 500-mL round-bottomed flask is equipped with a Dean Stark, condenser, stir bar and gas inlet (N2 gas atmosphere). The flask is charged with of 1,2-cyclohexanedione (15.14 g, 135.00 mmol), morpholine (14.82 g, 170.10 mmol) and toluene (330 mL). The resulting yellow solution is heated to reflux for 5 hours. Heating is stopped and about 3.0 mL of water are collected on the Dean Stark. The brown solution is decanted away from a thick oil and rinsed with toluene. The solution is concentrated under high vacuum to afford 23.33 g (95.34% yield) of title compound of Preparation 2 as a brown solid.

Workup

  1. customSynthesis
  2. customA 500-mL round-bottomed flask is equipped with a Dean Stark, condenser
  3. temperatureThe resulting yellow solution is heated
  4. temperatureto reflux for 5 hours
  5. temperatureHeating
  6. customabout 3.0 mL of water are collected on the Dean Stark
  7. customThe brown solution is decanted away from a thick oil
  8. washrinsed with toluene
  9. concentrationThe solution is concentrated under high vacuum
  10. customto afford

Sources & evidence

ORD record
ord-427f27a487294c78bfa30e9382f64998
Source dataset
uspto-grants-2013_02
Patent number
US08372927B2

Reaction notes

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