N-(4-Bromobutyl)phthalimide → 4-Amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamide

HRID 344280Notes

Reaction equation

HRID 344280 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.Br[CH2:24][CH2:25][CH2:26][CH2:27][N:28]1[C:32](=[O:33])[C:31]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:30]2[C:29]1=[O:38]>>[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]([CH2:24][CH2:25][CH2:26][CH2:27][N:28]3[C:32](=[O:33])[C:31]4[C:30](=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:29]3=[O:38])[CH2:16][CH2:17]2)=[O:9])=[C:6]([O:21][CH3:22])[CH:5]=1

Participants

3

Reactant 2

HCID 93575N-(4-Bromobutyl)phthalimideHCID 699663304-amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride

Product 1

HCID 539169944-Amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamideYield 40.6%

Procedure

4-Amino-5-chloro-2-methoxy-N-(piperidin-4-ylmethyl)benzamide dihydrochloride (17.0 g) and N-(4-bromobutyl)phthalimide (15.8 g) were reacted and treated in the same manner as in Preparation Example 150 to give 9.3 g of 4-amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1 H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamide.

Workup

  1. additiontreated in the same manner as in Preparation Example 150

Sources & evidence

ORD record
ord-e48d2e054b4f4f26a5ff0d8781e3c97e
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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