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Isopropanol → 7-methoxy-4-methyl-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-one

HRID 22325
Notes
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Reaction equation

HRID 22325 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([O:22][CH3:23])=[CH:12][C:13]2[O:18][C:17](=[O:19])[CH:16]=[C:15]([CH3:20])[C:14]=2[CH:21]=1)(=O)=O.[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)(C)C.C([O-])(=O)/C=C/C([O-])=O>C(O)C>[CH3:23][O:22][C:11]1[C:10]([O:9][CH2:8][CH2:7][CH2:6][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:14]2[C:15]([CH3:20])=[CH:16][C:17](=[O:19])[O:18][C:13]=2[CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 698734-PhenylpiperidineHCID 5460307FumarateHCID 199276896-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-methyl-2H-1-benzopyran-2-one

Product 1

HCID 199276477-methoxy-4-methyl-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-oneYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Method B (26 h at 50° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-4-methyl-2H-1-benzopyran-2-one (example 74) and 4-phenylpiperidine; yield 77%; fusion point 141°-143° C. (from isopropanol and ethanol). Fumarate: method E; yield 89%; fusion point 221°-223° C. (from ethanol).

Workup

  1. customMethod B (26 h at 50° C.)

Sources & evidence

ORD record
ord-139cda73f5df4923b379b1bd496e259a
Source dataset
uspto-grants-1995_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05428038

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes