Water → HCID 4788964, compound

HRID 1919163Notes

Reaction equation

HRID 1919163 reaction equation
[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C([O-])([O-])=O.[K+].[K+].Br[C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[N:20][CH:21]=1.O>CS(C)=O>[CH3:1][N:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:16]2[CH:21]=[N:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2283491-MethylhomopiperazineHCID 8176205-Bromo-2-nitropyridine

Product 1

HCID 4788964HCID 4788964, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 1-methyl-1,4-diazepane (1 g, 8.8 mmol) in DMSO (20 mL) were added K2CO3 (2.4 g, 18 mmol) and 5-bromo-2-nitropyridine (51-7) (1.78 g, 8.8 mmol). The mixture was stirred at 65° C. for overnight. It was allowed to cool to room temperature and poured into water. The resulting solid was collected and dried under vacuum. The solid was further purified by flash column eluting with 3:1 petroleum ether/ethyl acetate and then methylene chloride to give 338a as a yellow solid (800 mg, 69%). MS: [M+H]+ 236.

Workup

  1. temperatureto cool to room temperature
  2. customThe resulting solid was collected
  3. customdried under vacuum
  4. customThe solid was further purified by flash column
  5. washeluting with 3:1 petroleum ether/ethyl acetate

Sources & evidence

ORD record
ord-a0d53a92d8c241b5a67ba97aec520906
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…