Dichloromethane → 4-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)-piperidine hydrochloride

HRID 863502Notes

Reaction equation

HRID 863502 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)(OC(C)(C)C)=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:29][CH:30]1[CH2:48][C:34]2[C:35]3[NH:36][C:37](=[O:47])[C:38](=[O:46])[NH:39][C:40]=3[CH:41]=[C:42]([N+:43]([O-:45])=[O:44])[C:33]=2[CH2:32][CH2:31]1.FC(F)(F)C(O)=O.C(Cl)[Cl:57]>O1CCCC1.CN(C)C=O.C(N(CC)CC)C>[ClH:57].[N+:43]([C:42]1[C:33]2[CH2:32][CH2:31][CH:30]([NH:29][C:14]([CH:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[O:16])[CH2:48][C:34]=2[C:35]2[NH:36][C:37](=[O:47])[C:38](=[O:46])[NH:39][C:40]=2[CH:41]=1)([O-:45])=[O:44]

Participants

9

Reactant 5

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 682631,1'-CarbonyldiimidazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 196962049-Amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione

Product 1

HCID 196961494-(6-Nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydrobenzo[f]quinoxaline-9-ylcarbamoyl)-piperidine hydrochloride

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of N-Boc-piperidine-4-carboxylic acid (0.92 g, 4 mmol) and carbonyldiimidazole (0.65 g, 4 mmol) in 10 mL tetrahydrofuran was heated at reflux for 15 min. The mixture was added to the starting amine (Example 15, 0.6 g, 2 mmol) in 10 mL dimethylformamide and heated at 70° C. for 30 min. Triethylamine (0.4 g) was added and the mixture heated an additional 18 h. The solvent was evaporated and the yellow solid was washing with tetrahydrofuran, collected by filtration and dried to give 0.74 g. The solid was suspended in 50 mL methylene chloride, cooled in an icebath and treated with trifluoroacetic acid (1 g). After evaporating the solvent, the solid was washed with ether and acetone mixture and dried. Calc'd for C18H21N5O5.1.5HCl.H2O: C, 40.82; H, 4.57; N, 13.22; found-C, 40.35; H, 4.70; N, 12.91.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 min
  3. temperaturethe mixture heated an additional 18 h
  4. customThe solvent was evaporated
  5. washthe yellow solid was washing with tetrahydrofuran
  6. filtrationcollected by filtration
  7. customdried
  8. customto give 0.74 g
  9. temperaturecooled in an icebath
  10. customAfter evaporating the solvent
  11. washthe solid was washed with ether and acetone mixture
  12. customdried

Sources & evidence

ORD record
ord-4f48ac3c43a34b48bef207f9d89b1cb1
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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