2-(2-Bromoethyl)-2-phenyl-1,3-dioxolane → 4-amino-5-chloro-N-((1-(3,3-ethylenedioxy-3-phenylpropyl)piperidin-4-yl)methyl)-2-methoxybenzamide

HRID 344543Notes

Reaction equation

HRID 344543 reaction equation
Cl.Cl.[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1.[CH2:23]1[CH2:36][O:35][C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([CH2:26][CH2:27]Br)[O:24]1>>[NH2:3][C:4]1[C:19]([Cl:20])=[CH:18][C:7]([C:8]([NH:10][CH2:11][CH:12]2[CH2:13][CH2:14][N:15]([CH2:27][CH2:26][C:25]3([O:24][CH2:23][CH2:36][O:35]3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:16][CH2:17]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1

Participants

3

Reactant 2

HCID 137641292-(2-Bromoethyl)-2-phenyl-1,3-dioxolaneHCID 699663304-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride

Product 1

HCID 545659284-amino-5-chloro-N-((1-(3,3-ethylenedioxy-3-phenylpropyl)piperidin-4-yl)methyl)-2-methoxybenzamideYield 99.9%

Procedure

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (7.2 g) and 3,3-ethylenedioxy-3-phenylpropyl bromide (6.0 g) were reacted and treated in the same manner as in Example 172 to give 9.2 g of 4-amino-5-chloro-N-((1-(3,3-ethylenedioxy-3-phenylpropyl)piperidin-4-yl)methyl)-2-methoxybenzamide.

Workup

  1. additiontreated in the same manner as in Example 172

Sources & evidence

ORD record
ord-50f9134b598c4d1b93f0d588118ac679
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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