p-Toluenesulfonic acid → HCID 67696440, compound

HRID 1609392Notes

Reaction equation

HRID 1609392 reaction equation
[C:1](Cl)(=O)[C:2](Cl)=[O:3].[C:7]([O:10][CH2:11][CH:12]1[CH2:24][CH2:23][N:15]2[C:16]3[C:21]([CH:22]=[C:14]2[CH2:13]1)=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:9])[CH3:8].C(N(CC)CC)C.Cl.[NH:33]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:35]([CH2:42][C:43](=[NH:48])[O:44]C(C)C)=[CH:34]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl.C1(C)C=CC=CC=1>[C:7]([O:10][CH2:11][CH:12]1[CH2:24][CH2:23][N:15]2[C:16]3[C:21]([C:22]([C:1]4[C:2](=[O:3])[NH:44][C:43](=[O:48])[C:42]=4[C:35]4[C:36]5[C:41](=[CH:40][CH:39]=[CH:38][CH:37]=5)[NH:33][CH:34]=4)=[C:14]2[CH2:13]1)=[CH:20][CH:19]=[CH:18][CH:17]=3)(=[O:9])[CH3:8]

Participants

8

Reactant 5

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 14954045HCID 14954045, compoundHCID 20084644HCID 20084644, compound

Product 1

HCID 67696440HCID 67696440, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

165 mg (1.38 mmol) of oxalyl chloride were added to a stirred solution of 300 mg (1.24 mmol) of 8-acetoxymethyl-6,7,8,9-tetrahydropyrido[1,2-a]indole in 50 ml of dichloromethane at 0° C. The resulting solution was stirred for 15 minutes and the solvent was removed by evaporation. The residue was dissolved in 30 ml of toluene and added dropwise to a stirred solution of 496 mg (4.96 mmol) of triethylamine and mg (1.31 mmol) of isopropyl 3-indoleacetimidate hydrochloride in 20 ml of toluene. After 18 hours, 1.16 g (6.2 mmol) of p-toluenesulfonic acid were added and stirring was continued for 1 hour. The mixture was then partitioned between dichloromethane and water. The organic phase was dried over sodium sulfate and evaporated to dryness. The residue was purified by flash chromatography on silica gel using ethyl acetate/petroleum ether (1:1) for the elution to give 170 mg (38%) of 3-[8-(acetoxymethyl) -6,7,8,9-tetrahydropyrido[1,2-a]indol-10-yl]-4-[3-indolyl)-1H-pyrrole-2,5-dione in the form of an orange colored solid of melting point 264°-265° C.

Workup

  1. customthe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in 30 ml of toluene
  3. waitAfter 18 hours
  4. stirringstirring
  5. waitwas continued for 1 hour
  6. customThe mixture was then partitioned between dichloromethane and water
  7. dry with materialThe organic phase was dried over sodium sulfate
  8. customevaporated to dryness
  9. customThe residue was purified by flash chromatography on silica gel
  10. washfor the elution

Sources & evidence

ORD record
ord-1f6073b1febc44cd89158fd842ee643b
Source dataset
uspto-grants-1995_03
Patent number
US05399712

Reaction notes

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