1-[2-(4-Bromo-2-methylphenoxy)ethyl]pyrrolidine → 1-[2-[2-Methyl-4-[6-hydroxy-3-[[3-methyl-4-[(1-pyrrolidinyl)methyl]phenyl]methyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine Dioxalate

HRID 1070325Notes

Reaction equation

HRID 1070325 reaction equation
[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[OH:13][C:14]1[CH:15]=[CH:16][C:17]2[C:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][N:30]4[CH2:34][CH2:33][CH2:32][CH2:31]4)=[C:25]([CH3:35])[CH:24]=3)=[C:20](C3C=CC(OCCC4CCCN4)=NC=3)[S:19][C:18]=2[CH:50]=1.[N:51]1([CH2:56][CH2:57][O:58][C:59]2[CH:64]=[CH:63][C:62](Br)=[CH:61][C:60]=2[CH3:66])[CH2:55][CH2:54][CH2:53][CH2:52]1>>[C:1]([OH:6])(=[O:5])[C:2]([OH:4])=[O:3].[C:7]([OH:12])(=[O:11])[C:8]([OH:10])=[O:9].[CH3:66][C:60]1[CH:61]=[C:62]([C:20]2[S:19][C:18]3[CH:50]=[C:14]([OH:13])[CH:15]=[CH:16][C:17]=3[C:21]=2[CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][N:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[C:25]([CH3:35])[CH:24]=2)[CH:63]=[CH:64][C:59]=1[O:58][CH2:57][CH2:56][N:51]1[CH2:55][CH2:54][CH2:53][CH2:52]1

Participants

3

Reactant 2

HCID 8032231-[2-(4-Bromo-2-methylphenoxy)ethyl]pyrrolidineHCID 86757087HCID 86757087, compound

Product 1

HCID 867570861-[2-[2-Methyl-4-[6-hydroxy-3-[[3-methyl-4-[(1-pyrrolidinyl)methyl]phenyl]methyl]benzo[b]thiophen-2-yl]phenoxy]ethyl]pyrrolidine DioxalateYield 59%

Procedure

The title compound was prepared from 6-benzyloxy-2-(dimethylamino)benzo[b]thiophen-3-yl 3-methyl-4-[(1-pyrrolidinyl)methyl]phenyl ketone (Example 124, Part C) and 4-bromo-2-methylphenyl 2-(1-pyrrolidinyl)ethyl ether (Part A) in 59% yield after PrepLC (SiO2; gradient of 85:10:5 to 75:20:5 hexanes-THF-TEA) by essentially following the procedure detailed in Example 123, Part A.

Sources & evidence

ORD record
ord-2f69573751ba427b8ab59364f4ec965b
Source dataset
uspto-grants-2001_06
Patent number
US06251921B1

Reaction notes

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