Morpholine → 4-((Morpholin-4-yl)methyl)benzonitrile

HRID 1181439Notes

Reaction equation

HRID 1181439 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH2:7]Br)=[CH:5][CH:4]=1)#[N:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1>CC#N>[N:11]1([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 2168644-((Morpholin-4-yl)methyl)benzonitrileYield 68%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-cyanobenzylbromide (1.0 g, 5.1 mmol) in MeCN (10 ml) was added morpholine (0.44 g, 0.44 ml, 5.1 mmol) and the reaction was stirred at room temperature for 1 h. The precipitate was filtered off and partioned between CH2Cl2 and NaOH (2M). The organic layer was separated, dried over MgSO4 and dried to give the desired nitrile (0.70 g, 68%).

Workup

  1. filtrationThe precipitate was filtered off
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customdried

Sources & evidence

ORD record
ord-c03e08bb546d4897940e0340369484ed
Source dataset
uspto-grants-2007_10
Patent number
US07285563B2

Reaction notes

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