tert-Butyl methyl ether → 6-(1-methylethoxy)-7-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-one

HRID 22316

Reaction equation

HRID 22316 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:20]([O:21][CH:22]([CH3:24])[CH3:23])=[CH:19][C:13]2[CH:14]=[CH:15][C:16](=[O:18])[O:17][C:12]=2[CH:11]=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.CC(OC)(C)C.C([O-])(=O)/C=C/C([O-])=O>CC(C)=O.C(O)C>[CH3:23][CH:22]([O:21][C:20]1[C:10]([O:9][CH2:8][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:11][C:12]2[O:17][C:16](=[O:18])[CH:15]=[CH:14][C:13]=2[CH:19]=1)[CH3:24]

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 698734-PhenylpiperidineHCID 5460307FumarateHCID 199277007-[3-(methanesulfonyloxy)propoxy]-6-(1-methylethoxy)-2H-1-benzopyran-2-one

Product 1

HCID 199277226-(1-methylethoxy)-7-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-oneYield 69%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

Method B (24 h at 60° C.); starting materials: 7-[3-(methanesulfonyloxy)propoxy]-6-(1-methylethoxy)-2H-1-benzopyran-2-one (example 73) and 4-phenylpiperidine; yield 69%; fusion point 86°-87° C. (from TBME). Fumarate: method E; yield 90%; fusion point 164°-167° C. (from ethanol and acetone).

Workup

  1. customMethod B (24 h at 60° C.)

Sources & evidence

ORD record
ord-839f4529654e48c7bbcee0290e2694f8
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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