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

HRID 22342Notes

Reaction equation

HRID 22342 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([O:24][CH3:25])=[CH:12][C:13]2[O:18][C:17](=[O:19])[C:16]3[CH2:20][CH2:21][CH2:22][C:15]=3[C:14]=2[CH:23]=1)(=O)=O.[C:26]1([CH:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(O)(C)C.C([O-])(=O)/C=C/C([O-])=O>C(O)C>[CH3:25][O:24][C:11]1[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:35]2[CH2:36][CH2:37][CH:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:33][CH2:34]2)=[CH:23][C:14]2[C:15]3[CH2:22][CH2:21][CH2:20][C:16]=3[C:17](=[O:19])[O:18][C:13]=2[CH:12]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 698734-PhenylpiperidineHCID 5460307FumarateHCID 199276622,3-dihydro-8-[3-(methanesulfonyloxy)propoxy]-7-methoxy-cyclopenta[c][1]-benzopyran-4(1H)-one

Product 1

HCID 199276462,3-dihydro-7-methoxy-8-[3-(4-phenyl-1-piperidinyl)propoxy]cyclopenta[c][1]benzopyran-4(1H)-oneYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Method B (60 h at 25° C.); starting materials: 2,3-dihydro-8-[3-(methanesulfonyloxy)propoxy]-7-methoxy-cyclopenta[c][1]-benzopyran-4(1H)-one (example 82) and 4-phenylpiperidine; yield 65%; fusion point 164°-166° C. (from isopropanol). Fumarate: method E; yield 86%; fusion point 195°-198° C. (from ethanol).

Workup

  1. customMethod B (60 h at 25° C.)

Sources & evidence

ORD record
ord-dba128891fca4621af94e618a5af991d
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

Loading…