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

HRID 22315

Reaction equation

HRID 22315 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:20]([O:21][CH3:22])=[CH:19][C:13]2[CH:14]=[CH:15][C:16](=[O:18])[O:17][C:12]=2[CH:11]=1)(=O)=O.[C:23]1([CH:29]2[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>C(O)(C)C>[CH3:22][O:21][C:20]1[C:10]([O:9][CH2:8][CH2:7][CH2:6][N:32]2[CH2:33][CH2:34][CH:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:30][CH2:31]2)=[CH:11][C:12]2[O:17][C:16](=[O:18])[CH:15]=[CH:14][C:13]=2[CH:19]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 698734-PhenylpiperidineHCID 199276577-[3-(methanesulfonyloxy)propoxy]-6-methoxy-2H-1-benzopyran-2-one

Product 1

HCID 199277376-methoxy-7-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-oneYield 73%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Method B (20 h at 60° C.); starting materials: 7-[3-(methanesulfonyloxy)propoxy]-6-methoxy-2H-1-benzopyran-2-one (example 68) and 4-phenylpiperidine; yield 73%; fusion point 97°-99° C. (from isopropanol). Hydrochloride: method G; yield 93%; fusion point 198°-200° C. (from isopropanol).

Workup

  1. customMethod B (20 h at 60° C.)

Sources & evidence

ORD record
ord-074ad729d54a49d0a78cc3cd3d689108
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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