Hydrazine hydrate (1:1) → 4-Amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide

HRID 344389

Reaction equation

HRID 344389 reaction equation
O.NN.[NH2:4][C:5]1[C:36]([Cl:37])=[CH:35][C:8]([C:9]([NH:11][CH2:12][CH:13]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][N:24]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:15][CH2:14]2)=[O:10])=[C:7]([O:38][CH3:39])[CH:6]=1>C(O)C>[NH2:4][C:5]1[C:36]([Cl:37])=[CH:35][C:8]([C:9]([NH:11][CH2:12][CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[CH2:17][CH2:18]2)=[O:10])=[C:7]([O:38][CH3:39])[CH:6]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 543795694-amino-5-chloro-N-(1-(5-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)pentyl)piperidin-4-ylmethyl)-2-methoxybenzamide

Product 1

HCID 540083634-Amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamideYield 82.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (11.3 ml) was added to a solution of 4-amino-5-chloro-N-(1-(5-(2,3-dihydro-1,3-dioxo-1 H-isoindol-2-yl)pentyl)-piperidin-4-ylmethyl)-2-methoxybenzamide (60 g) in ethanol (0.6 L), and the mixture was refluxed under heating for 4 hr. The precipitated crystals were filtered off, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give 37.0 g of 4-amino-N-(1-(5-aminopentyl)piperidin-4-ylmethyl) -5-chloro-2-methoxybenzamide.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 4 hr
  3. filtrationThe precipitated crystals were filtered off
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e93f889a6b074315999bb4143df17942
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Linked notes

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