Isopropanol → HCID 19696323, compound

HRID 863684Notes

Reaction equation

HRID 863684 reaction equation
C(O[C:6]([N:8]1[CH2:37][CH2:36][N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]([C:19]3[C:20](=O)[O:21][C:22](=[O:34])[C:23]=3[C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH3:33])[CH:25]=3)=[C:10]2[CH2:9]1)=[O:7])(C)(C)C.C([N:40](CC)CC)C.ClC(O[C:49]1[CH:54]=CC=C[CH:50]=1)=O.[CH:55]([OH:58])([CH3:57])[CH3:56]>ClCCl.N.O>[O:58]([C:6]([N:8]1[CH2:37][CH2:36][N:11]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=3[C:18]([C:19]3[C:20](=[O:21])[NH:40][C:22](=[O:34])[C:23]=3[C:24]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:26]([CH3:33])[CH:25]=3)=[C:10]2[CH2:9]1)=[O:7])[C:55]1[CH:57]=[CH:54][CH:49]=[CH:50][CH:56]=1

Participants

8

Reactant 4

HCID 3776IsopropanolHCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 10391175HCID 10391175, compound

Product 1

HCID 19696323HCID 19696323, compound

Reagents, catalysts & solvents 3

HCID 222AmmoniaSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 100 mg of the pyrroledione product of Example 20 in 10 ml of dichloromethane was treated under nitrogen with 0.08 ml of triethylamine and 86 mg of phenyl chloroformate. The mixture was stirred for 2 hours and then the solvent was evaporated. Chromatography of the residue on silica gel with ethyl acetate/n-hexane (1:1) gave a gum which was dissolved in a mixture of 5 ml of isopropanol and 10 ml of 33% aqueous ammonia. The mixture was diluted with water and extracted with dichloromethane. The combined dichloromethane extracts were dried and evaporated. Crystallization of the residue from ethyl acetate/n-hexane gave 45 mg of 3-[1,2,3,4-tetrahydro-2-(phenoxycarbonyl)pyrazino[1,2-a]indol-10-yl]-4-(1-methyl-3-indolyl)-1H-pyrrole-2,5-dione of melting point 160°-165° C.

Workup

  1. customthe solvent was evaporated
  2. customChromatography of the residue on silica gel with ethyl acetate/n-hexane (1:1) gave a gum which
  3. extractionextracted with dichloromethane
  4. dry with materialThe combined dichloromethane extracts were dried
  5. customevaporated
  6. customCrystallization of the residue from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-1b77249e48c04b8bb99d4c1f65b2997b
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

Loading…