4-Methylmorpholine → HCID 68838308, compound

HRID 2113916Notes

Reaction equation

HRID 2113916 reaction equation
[N+:1]([C:4]1[N:5]([CH2:9][C:10]([OH:12])=O)[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2].CN1CCOCC1.ClC(OCC(C)C)=O.Cl.[CH2:29]([NH2:32])[CH:30]=[CH2:31]>C1COCC1>[N+:1]([C:4]1[N:5]([CH2:9][C:10]([NH:32][CH2:29][CH:30]=[CH2:31])=[O:12])[CH:6]=[CH:7][N:8]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 79724-Methylmorpholine2×HCID 62365Isobutyl chloroformateHCID 82291Allylamine hydrochlorideHCID 3275442-(2-Nitroimidazol-1-yl)acetic acid

Product 1

HCID 68838308HCID 68838308, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(2-nitro-1H-imidazol-1-yl)acetic acid (1.71 g, 10 mmol) was added to N-methylmorpholine (1.01 g, 10 mmol) in 150 ml of dry THF under nitrogen at 0° C. and stirred for 10 minutes until completely dissolved. Isobutyl chloroformate (1.43 mL 11 mmol) added. After 30 minutes, allylamine hydrochloride (1.03 g, 11 mmol) and N-methylmorpholine (1.21 g, 12 mmol) added to the solution and the mixture stirred at room temperature overnight. The solution was then filtered and the organic solvent was evaporated to give a pale yellow solid. Purification by chromatography (silica gel, CH3OH/CHCl3=10:1) gave a white solid (1 g, 48%).

Workup

  1. dissolutionuntil completely dissolved
  2. waitAfter 30 minutes
  3. stirringthe mixture stirred at room temperature overnight
  4. filtrationThe solution was then filtered
  5. customthe organic solvent was evaporated
  6. customto give a pale yellow solid
  7. customPurification by chromatography (silica gel, CH3OH/CHCl3=10:1)

Sources & evidence

ORD record
ord-60c788edcefb4b0bb3b7f3c9823155de
Source dataset
uspto-grants-2008_10
Patent number
US07432295B2

Reaction notes

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