4-Phenylpiperidine → 2,3-dihydro-7-methoxy-8-[2-(4-phenyl-1-piperidinyl)ethoxy]cyclopenta[c][1]benzopyran-4(1H)-one

HRID 22341Notes

Reaction equation

HRID 22341 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[C:10]([O:23][CH3:24])=[CH:11][C:12]2[O:17][C:16](=[O:18])[C:15]3[CH2:19][CH2:20][CH2:21][C:14]=3[C:13]=2[CH:22]=1)(=O)=O.[C:25]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])(=O)/C=C/C([O-])=O>C(O)(C)C.C(O)C>[CH3:24][O:23][C:10]1[C:9]([O:8][CH2:7][CH2:6][N:34]2[CH2:35][CH2:36][CH:31]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:32][CH2:33]2)=[CH:22][C:13]2[C:14]3[CH2:21][CH2:20][CH2:19][C:15]=3[C:16](=[O:18])[O:17][C:12]=2[CH:11]=1

Participants

6

Reactant 3

HCID 698734-PhenylpiperidineHCID 5460307FumarateHCID 199277162,3-dihydro-8-[2-(methanesulfonyloxy)ethoxy]-7-methoxy-cyclopenta[c][1]-benzopyran-4(1H)-one

Product 1

HCID 199276922,3-dihydro-7-methoxy-8-[2-(4-phenyl-1-piperidinyl)ethoxy]cyclopenta[c][1]benzopyran-4(1H)-oneYield 93%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent2×

Procedure

Method B (16 h at 60° C.); starting materials: 2,3-dihydro-8-[2-(methanesulfonyloxy)ethoxy]-7-methoxy-cyclopenta[c][1]-benzopyran-4(1H)-one (example 81) and 4-phenylpiperidine; yield 93%; fusion point 150°-152° C. (from isopropanol). Fumarate: method E; yield 84%; fusion point 185°-187° C. (from ethanol and isopropanol).

Workup

  1. customMethod B (16 h at 60° C.)

Sources & evidence

ORD record
ord-ae92c5fb9bf44028bd0d27339139ab34
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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