4-Phenylpiperidine → 7-methoxy-3,4-dimethyl-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-one

HRID 22327

Reaction equation

HRID 22327 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([O:23][CH3:24])=[CH:12][C:13]2[O:18][C:17](=[O:19])[C:16]([CH3:20])=[C:15]([CH3:21])[C:14]=2[CH:22]=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.C([O-])(=O)/C=C/C([O-])=O>CO.C(O)C.C(O)(C)C>[CH3:24][O:23][C:11]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:22][C:14]2[C:15]([CH3:21])=[C:16]([CH3:20])[C:17](=[O:19])[O:18][C:13]=2[CH:12]=1

Participants

7

Reactant 3

HCID 698734-PhenylpiperidineHCID 5460307FumarateHCID 199276786-[3-(methanesulfonyloxy)propoxy]-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one

Product 1

HCID 199276817-methoxy-3,4-dimethyl-6-[3-(4-phenyl-1-piperidinyl)propoxy]-2H-1-benzopyran-2-oneYield 64%

Reagents, catalysts & solvents 3

HCID 702EthanolSolvent2×HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

Method A (9 h at 60° C.); starting materials: 6-[3-(methanesulfonyloxy)propoxy]-7-methoxy-3,4-dimethyl-2H-1-benzopyran-2-one (example 75) and 4-phenylpiperidine; yield 64%; fusion point 152°-153° C. (from ethanol and isopropanol). Fumarate (×0.5 C4H4O4): method E; yield 92%; fusion point 209°-210° C. (from ethanol and methanol).

Workup

  1. customMethod A (9 h at 60° C.)

Sources & evidence

ORD record
ord-27d533dd5f99403a86ddd4adb5d31e9f
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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