1-(3-Chloropropyl)-4-phenylpiperidine → 7-methoxy-6-[3-(4-phenyl-1-piperidinyl)propoxy]-4-(trifluoromethyl)-2H-1-benzopyran-2-one

HRID 22329

Reaction equation

HRID 22329 reaction equation
[OH:1][C:2]1[C:3]([O:17][CH3:18])=[CH:4][C:5]2[O:10][C:9](=[O:11])[CH:8]=[C:7]([C:12]([F:15])([F:14])[F:13])[C:6]=2[CH:16]=1.Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.C([O-])(=O)/C=C/C([O-])=O>CC(OC)(C)C.C(O)C.CO>[CH3:18][O:17][C:3]1[C:2]([O:1][CH2:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:27][CH2:28]2)=[CH:16][C:6]2[C:7]([C:12]([F:13])([F:14])[F:15])=[CH:8][C:9](=[O:11])[O:10][C:5]=2[CH:4]=1

Participants

7

Reactant 3

HCID 2036891-(3-Chloropropyl)-4-phenylpiperidineHCID 5460307FumarateHCID 199277396-hydroxy-7-methoxy-4-(trifluoromethyl)-2H-1-benzopyran-2-one

Product 1

HCID 199276957-methoxy-6-[3-(4-phenyl-1-piperidinyl)propoxy]-4-(trifluoromethyl)-2H-1-benzopyran-2-oneYield 45%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Method D (3 h at 85° C.); starting materials: 6-hydroxy-7-methoxy-4-(trifluoromethyl)-2H-1-benzopyran-2-one (example 104) and 1-(3-chloropropyl)-4-phenylpiperidine; yield 45%; fusion point 125°-126° C. (from TBME and methanol). Fumarate: method E; yield 59%; fusion point 176°-179° C. (from ethanol and TBME).

Workup

  1. customMethod D (3 h at 85° C.)

Sources & evidence

ORD record
ord-ee803333f37a47e09dae10cb3370c666
Source dataset
uspto-grants-1995_06
Patent number
US05428038

Linked notes

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