Hydrochloric Acid → 1-(5-Bromopyridin-2-yl)-1,4-diazepane

HRID 1640424Notes

Reaction equation

HRID 1640424 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:15][CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]2)=[N:7][CH:8]=1>C(O)(C)C.O1CCOCC1.C(O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[N:7][CH:8]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 602095661,1-Dimethylethyl 4-(5-bromo-2-pyridinyl)-1,4-diazepane-1-carboxylate

Product 1

HCID 167847331-(5-Bromopyridin-2-yl)-1,4-diazepaneYield 117.1%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

6 ml of a solution of hydrogen chloride (6N) in isopropanol are added to a solution of 1.63 g (4.4 mmol) of 1,1-dimethylethyl 4-(5-bromo-2-pyridyl)-1,4-diazepane-1-carboxylate, obtained in step 11.1, in 12 ml of dioxane and 4 ml of ethanol. This reaction mixture is maintained at 70° C. for 3 hours. The mixture is allowed to cool to room temperature and is then concentrated under reduced pressure. 1.32 g of a white solid are obtained after crystallization from acetone. These crystals are taken up in 10 ml of dichloromethane and the reaction medium is basified to pH=14, by adding 28% ammonia solution. The organic phase is recovered by filtration through a hydrophobic cartridge and the filtrate is concentrated under reduced pressure. 0.96 g of product is obtained in the form of an oil, and is used without further purification in the following step.

Workup

  1. temperatureto cool to room temperature
  2. concentrationis then concentrated under reduced pressure

Sources & evidence

ORD record
ord-5c6a86dd77024bb7abecc505e8c77aaa
Source dataset
uspto-grants-2012_02
Patent number
US08114866B2

Reaction notes

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