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

HRID 344237Notes

Reaction equation

HRID 344237 reaction equation
[NH2:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][N:20]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:12][CH2:11]2)=[O:7])=[C:4]([O:34][CH3:35])[CH:3]=1.O.NN>C(O)C>[NH2:1][C:2]1[C:32]([Cl:33])=[CH:31][C:5]([C:6]([NH:8][CH2:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][CH2:18][CH2:19][NH2:20])[CH2:14][CH2:15]2)=[O:7])=[C:4]([O:34][CH3:35])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 539169944-Amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamide

Product 1

HCID 541388784-amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamideYield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Amino-5-chloro-N-(1-(4-(2,3-dihydro-1,3-dioxo-1H-isoindol-2-yl)butyl)piperidin-4-ylmethyl)-2-methoxybenzamide (8.3 g) was dissolved in ethanol (100 ml) and hydrazine hydrate (1.1 ml) was added at room temperature with stirring. The mixture was refluxed with stirring for 3 hr. The precipitated crystals were filtered off and the filtrate was concentrated under reduced pressure to give 4.4 g of 4-amino-N-(1-(4-aminobutyl)piperidin-4-ylmethyl)-5-chloro-2-methoxybenzamide.

Workup

  1. temperatureThe mixture was refluxed
  2. stirringwith stirring for 3 hr
  3. filtrationThe precipitated crystals were filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-cccadd240b6d4dd0b0e2e5566efacf07
Source dataset
uspto-grants-1999_01
Patent number
US05864039

Reaction notes

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