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

HRID 22335Notes

Reaction equation

HRID 22335 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[C:7]([O:24][CH3:25])=[CH:8][C:9]2[O:14][C:13](=[O:15])[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:11]([CH3:22])[C:10]=2[CH:23]=1.[C:26]1([N: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>CC(C)=O>[CH3:25][O:24][C:7]1[C:6]([O:5][CH2:4][CH2:3][CH2:2][N:35]2[CH2:36][CH2:37][N:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:33][CH2:34]2)=[CH:23][C:10]2[C:11]([CH3:22])=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13](=[O:15])[O:14][C:9]=2[CH:8]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 70961-PhenylpiperazineHCID 5460307FumarateHCID 199276886-(3-chloropropoxy)-7-methoxy-4-methyl-3-phenyl-2H-1-benzopyran-2-one

Product 1

HCID 199276497-methoxy-4-methyl-3-phenyl-6-[3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-oneYield 66%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Method B (40 h at 50° C.); starting materials: 6-(3-chloropropoxy)-7-methoxy-4-methyl-3-phenyl-2H-1-benzopyran-2-one (example 79) and 1-phenylpiperazine; yield 66%; fusion point 168°-170° C. (from isopropanol). Fumarate: method E; yield 95%; fusion point 219°-221° C. (from acetone).

Workup

  1. customMethod B (40 h at 50° C.)

Sources & evidence

ORD record
ord-09afacfa03cd4474812a8a3ecf12e3cc
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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