4-Phenylpiperidine → 2,3-dihydro-7-methoxy-8-[5-(4-phenyl-1-piperidinyl)pentyloxy]cyclopenta[c][1]benzopyran-4(1H)-one

HRID 22344Notes

Reaction equation

HRID 22344 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][O:7][C:8]1[C:9]([O:22][CH3:23])=[CH:10][C:11]2[O:16][C:15](=[O:17])[C:14]3[CH2:18][CH2:19][CH2:20][C:13]=3[C:12]=2[CH:21]=1.[C:24]1([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(=O)/C=C/C([O-])=O>CC(OC)(C)C.C(O)(C)C>[CH3:23][O:22][C:9]1[C:8]([O:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:33]2[CH2:34][CH2:35][CH:30]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:31][CH2:32]2)=[CH:21][C:12]2[C:13]3[CH2:20][CH2:19][CH2:18][C:14]=3[C:15](=[O:17])[O:16][C:11]=2[CH:10]=1

Participants

6

Reactant 3

HCID 698734-PhenylpiperidineHCID 5460307FumarateHCID 199276368-(5-bromopentyloxy)-2,3-dihydro-7-methoxycyclopenta[c][1]benzopyran-4(1H)-one

Product 1

HCID 199277182,3-dihydro-7-methoxy-8-[5-(4-phenyl-1-piperidinyl)pentyloxy]cyclopenta[c][1]benzopyran-4(1H)-oneYield 37%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolvent2×HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Method B (20 h at 80° C.); starting materials: 8-(5-bromopentyloxy)-2,3-dihydro-7-methoxy-cyclopenta[c][1]benzopyran-4(1H)-one (example 85) and 4-phenylpiperidine; yield 37%; fusion point 103°-105° C. (from isopropanol and TBME). Fumarate: method E; yield 94%; fusion point 176°-178° C. (from isopropanol and TBME).

Workup

  1. customMethod B (20 h at 80° C.)

Sources & evidence

ORD record
ord-1c7274b96f0b47aa88e9a7f1d1e0c0ba
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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