Sodium Carbonate → HCID 22169632, compound

HRID 1822721Notes

Reaction equation

HRID 1822721 reaction equation
[CH2:1]1[N:6]([C:7]2[C:12]([C:13]#[N:14])=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:5][CH2:4]OC1.Cl.[CH3:16][NH:17][OH:18].[C:19](=[O:22])([O-])[O-].[Na+].[Na+]>O.C(O)C>[OH:18][N:17]([CH3:16])[C:13](=[NH:14])[C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:6]1[CH2:1][CH2:19][O:22][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 77906N-methylhydroxylamine hydrochlorideHCID 27370122-Morpholinobenzonitrile

Product 1

HCID 22169632HCID 22169632, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirred solution of 2-(4-morpholino)benzonitrile (3.76 g, 20 mmol) and N-methylhydroxylamine hydrochloride (3.34 g, 40.0 mmol) in 1:1 water/ethanol (100 mL) was added sodium carbonate (2.12 g, 20 mmol) and the resulting mixture stirred at 90° C. overnight. After cooling and concentrating, the resulting residue was suspended in MeOH/CHCl3 (1:9). The insoluble solids were removed by filtration and concentration of the mother liquor gave the title product as an amber oil (3.8 g) that was carried on without further purification. LCMS calcd for C12H18N3O2 (M+H): 236.13; found: 236.31.

Workup

  1. temperatureAfter cooling
  2. concentrationconcentrating
  3. customThe insoluble solids were removed by filtration and concentration of the mother liquor

Sources & evidence

ORD record
ord-7f5e791320e7472792d4215a5727bbff
Source dataset
uspto-grants-2006_05
Patent number
US07037908B2

Reaction notes

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