2-Methoxyethylamine → HCID 28426087, compound

HRID 2410557Notes

Reaction equation

HRID 2410557 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].[C:6]([C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1)#[N:7]>C(#N)C>[CH3:1][O:2][CH2:3][CH2:4][NH:5][CH2:12][C:11]1[CH:14]=[CH:15][C:8]([C:6]#[N:7])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 869964-(Bromomethyl)benzonitrile

Product 1

HCID 28426087HCID 28426087, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-Methoxyethylamine (2.2 mL, 25.5 mmol) was added into a solution of 4-cyanobenzyl bromide (1.0 g, 5.1 mmol) in ACN (10 mL) and the resulting mixture was stirred at RT for 1 hour. The reaction mixture was concentrated under vacuum. The crude product was dissolved in EtOAc, and then washed with a saturated aqueous solution of NaHCO3 and brine, dried (MgSO4) and concentrated under vacuum to give the title compound (958 mg, 99%). LC/MS (Method B): 191.0 (M+H)+. HPLC (Method A) Rt 1.44 min (Purity: 93.4%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutionThe crude product was dissolved in EtOAc
  3. washwashed with a saturated aqueous solution of NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4ccc0c7f6f274285a455b90cf2972ee2
Source dataset
uspto-grants-2014_08
Patent number
US08815919B2

Reaction notes

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