Morpholine → 2-Methoxy-5-morpholin-4-ylmethyl-benzonitrile

HRID 1167328Notes

Reaction equation

HRID 1167328 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O1CCCC1>[CH3:12][O:11][C:6]1[CH:5]=[CH:4][C:3]([CH2:2][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:10][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 229961915-(Chloromethyl)-2-methoxybenzonitrile

Product 1

HCID 229962172-Methoxy-5-morpholin-4-ylmethyl-benzonitrileYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-chloromethyl-2-methoxy-benzonitrile (246 mg, 1.354 mmol, example 29) in tetrahydrofuran (10 mL) at room temperature was added morpholine (1.193 mL, 13.54 mmol). The reaction mixture was heated at reflux for 4 h. The reaction was concentrated in vacuo (with heating) to remove morpholine and tetrahydrofuran to afford 2-methoxy-5-morpholin-4-ylmethyl-benzonitrile as a yellow oil (311.2 mg, 99%). The crude product was used without further purification.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. concentrationThe reaction was concentrated in vacuo (with heating)
  4. customto remove morpholine and tetrahydrofuran

Sources & evidence

ORD record
ord-6bebd5ab91ac4184938f0debdedbeb45
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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