Hydrochloric Acid → (+/-)-6-{3-[4-(bis(4-fluorophenyl)hydroxymethyl)-1-piperidinyl]-2-hydroxypropoxy}-7-methoxy-2H-1-benzopyran-2-one

HRID 22323

Reaction equation

HRID 22323 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.[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:34]2[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=2)([OH:33])[CH:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:22][CH:21]=1.CO.Cl>C(O)C.C(O)(C)C.C(Cl)(Cl)Cl>[F:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]([C:34]2[CH:35]=[CH:36][C:37]([F:40])=[CH:38][CH:39]=2)([OH:33])[CH:27]2[CH2:28][CH2:29][N:30]([CH2:18][CH:16]([OH:17])[CH2:15][O:14][C:13]3[C:3]([O:2][CH3:1])=[CH:4][C:5]4[O:10][C:9](=[O:11])[CH:8]=[CH:7][C:6]=4[CH:12]=3)[CH2:31][CH2:32]2)=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 199276727-methoxy-6-(oxiranylmethoxy)-2H-1-benzopyran-2-one

Product 1

HCID 19927676(+/-)-6-{3-[4-(bis(4-fluorophenyl)hydroxymethyl)-1-piperidinyl]-2-hydroxypropoxy}-7-methoxy-2H-1-benzopyran-2-oneYield 45%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

Method C (5 d at 45° C.); starting materials: 7-methoxy-6-(oxiranylmethoxy)-2H-1-benzopyran-2-one and 4-[bis(4-fluorophenyl)hydroxymethyl]piperidine; yield 45%; fusion point 220°-221° C. (from methanol and chloroform). Hydrochloride: method G; yield 99%; fusion point 172°-174° C. (from isopropanol and ethanol).

Workup

  1. customMethod C (5 d at 45° C.)

Sources & evidence

ORD record
ord-27e1f705903044f48f64c5fe115171f8
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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