Triethylamine → Piperidine-4-carboxylic acid (6-nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoxalin-9-yl) amide

HRID 863489Notes

Reaction equation

HRID 863489 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=O)(C)(C)C.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.C(N(CC)CC)C>O1CCCC1.CN(C)C=O>[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

7

Reactant 4

HCID 8471TriethylamineHCID 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 19696150Piperidine-4-carboxylic acid (6-nitro-2,3-dioxo-1,2,3,4,7,8,9,10-octahydro-benzo[f]quinoxalin-9-yl) amideYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

N-t-butyloxycarbonylpiperidine-4-carboxylic acid (0.35 g, 1.5 mmol) and carbonyldiimidazole (0.24 g, 1.5 mmol) were refluxed in tetrahydrofuran (5 mL) for 15 min. The mixture was added to a solution of 9-amino-6-nitro-1,4,7,8,9,10-hexahydro-benzo[f]quinoxaline-2,3-dione (0.15 g, 1.5 mmol) in dimethylformamide (5 mL) and heated to 70° C. After 15 min, triethylamine (0.15 g, 1.5 mmol) was added and heating continued at 70° C. for 6 h. The solvent was removed by rotoevaporation in vacuo and the residue triturated with diethyl ether to form a solid. The solid was collected by filtration, washed with water and dried to give the crude product (0.23 g, 94% yield). For further purification, the solid was suspended and stirred in 2N HCl, and then filtered and dried. Anal. calc'd for C23H29N5O7.1.5 NaCl.H2O: C, 40.82; H, 4.57; N, 13.22; found-C, 40.35; H, 4.70:N, 12.91.

Workup

  1. temperatureheating
  2. waitcontinued at 70° C. for 6 h
  3. customThe solvent was removed by rotoevaporation in vacuo
  4. customthe residue triturated with diethyl ether
  5. customto form a solid
  6. filtrationThe solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-8eeca090c05140088523d726a2620d04
Source dataset
uspto-grants-1998_02
Patent number
US05721234

Reaction notes

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