1-[2-(4-Bromo-2-methoxyphenoxy)ethyl]pyrrolidine → HCID 86757088, compound

HRID 1070326Notes

Reaction equation

HRID 1070326 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[O:66][CH3:67])[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].[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]([C:62]3[CH:63]=[CH:64][C:59]([O:58][CH2:57][CH2:56][N:51]4[CH2:55][CH2:54][CH2:53][CH2:52]4)=[C:60]([O:66][CH3:67])[CH:61]=3)[S:19][C:18]=2[CH:50]=1

Participants

3

Reactant 2

HCID 229943381-[2-(4-Bromo-2-methoxyphenoxy)ethyl]pyrrolidineHCID 86757087HCID 86757087, compound

Product 1

HCID 86757088HCID 86757088, compoundYield 30%

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-methoxyphenyl 2-(1-pyrrolidinyl)ethyl ether (Part A) in 30% yield after PrepLC (SiO2; gradient of 80:15:5 to 70:25:5 hexanes-THF-TEA) by essentially following the procedure detailed in Example 123, Part A.

Sources & evidence

ORD record
ord-736fbb5143ce47a98ca6b299ee74627a
Source dataset
uspto-grants-2001_06
Patent number
US06251921B1

Reaction notes

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