Hydrochloric Acid → (+/-)-7-methoxy-6-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-one

HRID 22318Notes

Reaction equation

HRID 22318 reaction equation
[CH3:1][O:2][C:3]1[C:13]([O:14][CH2:15][CH:16]2[CH2:18][O:17]2)=[CH:12][C:6]2[CH:7]=[CH:8][C:9](=[O:11])[O:10][C:5]=2[CH:4]=1.[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.Cl>CO.C(O)C.C(O)(C)C>[CH3:1][O:2][C:3]1[C:13]([O:14][CH2:15][CH:16]([OH:17])[CH2:18][N:28]2[CH2:29][CH2:30][N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)=[CH:12][C:6]2[CH:7]=[CH:8][C:9](=[O:11])[O:10][C:5]=2[CH:4]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 70961-PhenylpiperazineHCID 199276727-methoxy-6-(oxiranylmethoxy)-2H-1-benzopyran-2-one

Product 1

HCID 19927697(+/-)-7-methoxy-6-[2-hydroxy-3-(4-phenyl-1-piperazinyl)propoxy]-2H-1-benzopyran-2-oneYield 99%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 3776IsopropanolSolvent2×

Procedure

Method C (5 d at 40° C.); starting materials: 7-methoxy-6-(oxiranylmethoxy)-2H-1-benzopyran-2-one and 1-phenylpiperazine; yield 99%; fusion point 160°-162° C. (from isopropanol and ethanol). Hydrochloride: method F; yield 78%; fusion point 222°-225° C. (from isopropanol, ethanol and methanol).

Workup

  1. customMethod C (5 d at 40° C.)

Sources & evidence

ORD record
ord-276aa49dfb0348d181a099581cff2403
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Reaction notes

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