Morpholine → HCID 19035983, compound

HRID 129450Notes

Reaction equation

HRID 129450 reaction equation
Cl[CH:2]1[C:14]2[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=2[C:8]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>O1CCCC1>[O:20]1[CH2:21][CH2:22][N:17]([CH:2]2[C:14]3[NH:13][C:12](=[O:15])[C:11](=[O:16])[NH:10][C:9]=3[C:8]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]2=3)[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 19035982HCID 19035982, compound

Product 1

HCID 19035983HCID 19035983, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9-Chloro-9H-indeno[1,2-b]pyrazine-2,3(1H, 4H)-dione (0.50 g, 2.13 mmol) was suspended in 5 ml of dry tetrahydrofuran, while cooling in an ice bath. Morpholine(0.37 ml, 4.27 mmol) dissolved in 2 ml of dry tetrahydrofuran was added over 2 min. After 1 hour the ice bath was removed and stirring was continued for 20 hours at room temperature. The precipitate was filtered off and washed with tetrahydrofuran, 10% acetic acid, water and dried to give 0.365 g of the crude product. Recrystallization from ethanol afforded 0.257 g (42%) of the title compound. M.p. 265°-267° C. 1H-NMR (DMSO-d6, δ): 2.47 (m, 2H), 2.61 (m, 2H), 3.56 (m, 4H), 4.54 (s, 1H), 7.13 (t, 1H), 7.3 (t, 1H), 7.47 (d, 1H), 7.53 (d, 1H), 11.8 (s, 1H), 12.25 (s, 1H).

Workup

  1. temperaturewhile cooling in an ice bath
  2. additionwas added over 2 min
  3. customAfter 1 hour the ice bath was removed
  4. filtrationThe precipitate was filtered off
  5. washwashed with tetrahydrofuran, 10% acetic acid, water
  6. customdried
  7. customto give 0.365 g of the crude product
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-6aca49cf423e43d58cad15c336579b9f
Source dataset
uspto-grants-1995_11
Patent number
US05468748

Reaction notes

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