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

HRID 22322

Reaction equation

HRID 22322 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.[OH:19][C:20]1([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.Cl>C(O)(C)C>[OH:17][CH:16]([CH2:18][N:23]1[CH2:24][CH2:25][C:20]([OH:19])([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:21][CH2:22]1)[CH2:15][O:14][C:13]1[C:3]([O:2][CH3:1])=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 963874-Phenylpiperidin-4-olHCID 199276727-methoxy-6-(oxiranylmethoxy)-2H-1-benzopyran-2-one

Product 1

HCID 19927673(+/-)-6-[2-hydroxy-3-(4-hydroxy-4-phenyl-1-piperidinyl)propoxy]-7-methoxy-2H-1-benzopyran-2-oneYield 69%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

Method C (3 d at 40° C.); starting materials: 7-methoxy-6-(oxiranylmethoxy)-2H-1-benzopyran-2-one and 4-hydroxy-4-phenylpiperidine; yield 69%; fusion point 155°-157° C. (from isopropanol). Hydrochloride: method G; yield 88%; fusion point 202°-203° C. (from isopropanol).

Workup

  1. customMethod C (3 d at 40° C.)

Sources & evidence

ORD record
ord-6c21ad51386049a890bf9e863962f865
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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