Sodium Carbonate → HCID 66888002, compound

HRID 252347Notes

Reaction equation

HRID 252347 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH2:9])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:16][O:17][CH2:18][CH2:19][CH2:20][C:21](Cl)=[O:22]>C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][NH:9][C:21](=[O:22])[CH2:20][CH2:19][CH2:18][O:17][CH3:16])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 127949894-Methoxybutanoyl chlorideHCID 49761678(5-Bromopyridin-2-yl)methanamine

Product 1

HCID 66888002HCID 66888002, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 9.35 g of C-(5-bromopyridin-2-yl)methylamine [17399-23-0] in 200 ml of ethyl acetate is admixed with 300 ml of saturated aqueous sodium carbonate solution. The reaction mixture is cooled to 0° C. in an ice bath and subsequently admixed dropwise with a solution of 4-methoxybutanoyl chloride [61882-39-1] in 100 ml of ethyl acetate. The reaction mixture is stirred at 0° C. over 1 hour. The phases are separated and the aqueous phase is extracted with 300 ml of ethyl acetate (2×). The combined organic phases are washed with 300 ml of brine, dried over sodium sulphate and concentrated by evaporation. The title compound is identified on the basis of the Rf value from the residue by means of flash chromatography (SiO2 60F).

Workup

  1. customThe phases are separated
  2. extractionthe aqueous phase is extracted with 300 ml of ethyl acetate (2×)
  3. washThe combined organic phases are washed with 300 ml of brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-4871c93f7c6946d5ad8fd09b06bb468a
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

Loading…