Sodium Carbonate → HCID 66888002, compound

HRID 2263533Notes

Reaction equation

HRID 2263533 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 60 F).

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-07dd200c5e944cce89a458de10e845dc
Source dataset
uspto-grants-2010_12
Patent number
US07851634B2

Reaction notes

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