Morpholine → HCID 59558570, compound

HRID 1921321Notes

Reaction equation

HRID 1921321 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10]Br)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(N(CC)CC)C>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 442031405-Bromo-2-(bromomethyl)benzonitrile

Product 1

HCID 59558570HCID 59558570, compoundYield 74.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5-Bromo-2-bromomethylbenzonitrile (2.50 g, 9.1 mmol) is added portionwise to a stirred solution of morpholine (828 μL, 9.5 mmol) and triethylamine (1.27 mL, 9.1 mmol) in methanol (2 mL). After 4 hr, the solvent is removed and the residue is suspended in water that is made basic with sodium hydroxide and then extracted with ethyl acetate. The extract is dried, filtered, and concentrated to give 5-bromo-2-(morpholin-4-yl)methylbenzonitrile (1.90 g, 74%) as a cream solid.

Workup

  1. customthe solvent is removed
  2. extractionextracted with ethyl acetate
  3. customThe extract is dried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-97029078feef4f5a96ce09f9e59535e8
Source dataset
uspto-grants-2012_05
Patent number
US08173682B2

Reaction notes

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