Hexahydro-1,4-diazepine → HCID 59548730, compound

HRID 1846638Notes

Reaction equation

HRID 1846638 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[C:9](Cl)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:6].[NH:19]1[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][C:8]1[C:9]([N:19]2[CH2:25][CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)=[N:10][CH:11]=[C:12]([Cl:14])[CH:13]=1)=[O:6]

Participants

4

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 86676282HCID 86676282, compound

Product 1

HCID 59548730HCID 59548730, compoundYield 66.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 0.500 g (1.66 mmol) of 3-chloro-N-(2,5-dichloro-pyridin-3-yl)-benzamide and 0.498 g (4.97 mmol) of homopiperazine in acetonitrile (5 mL) is heated at 175° C. in a microwave reactor for 90 minutes. The mixture is cooled to room temperature and concentrated under reduced pressure. The residue is purified by flash silica gel chromatography to give 0.390 g (66.8%) of 3-chloro-N-(5-chloro-2-[1,4]diazepan-1-yl-pyridin-3-yl)-benzamide as a red oil.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-f9353e85a3624800bd18bbc1b27c78e8
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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