Potassium Carbonate → HCID 67114629, compound

HRID 1844249Notes

Reaction equation

HRID 1844249 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:17][C@H:16]2[NH2:18])=[CH:11][CH:10]=1.Br[CH2:20][C:21]([NH2:23])=[O:22]>CN(C=O)C>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([C@@H:15]2[CH2:17][C@H:16]2[NH:18][CH2:20][C:21]([NH2:23])=[O:22])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 696322-BromoacetamideHCID 56683886(1R,2S)-2-(4-Bromo-phenyl)-cyclopropylamine hydrochloride

Product 1

HCID 67114629HCID 67114629, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of K2CO3 (3.48 g, 25.4 mmol, 2.1 equiv) in dry DMF (30 mL) a solution of (trans)-2-(4-bromophenyl)cyclopropanamine hydrochloride (3 g, 12.09 mmol, 1 equiv) in dry DMF (6 mL) was added at 0° C. and stirred for 10 min, then 2-bromoacetamide (1.82 g, 13.3 mmol, 1.1 equiv) was added and stirred at RT for 2 h. After completion, the reaction mixture was poured into ice water (50 mL) and extracted with EtOAc (2×50 mL). The combined extracts were washed with water (2×50 mL), brine (50 mL), dried over anhydrous Na2SO4, filtered and evaporated. The crude residue was purified by column chromatography (SiO2) using MeOH:CHCl3 (3:97) to get 2-((trans)-2-(4-bromophenyl)cyclopropylamino)acetamide (1 g, 31% yield) as a white solid.

Workup

  1. additionwas added at 0° C.
  2. stirringstirred at RT for 2 h
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined extracts were washed with water (2×50 mL), brine (50 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude residue was purified by column chromatography (SiO2)

Sources & evidence

ORD record
ord-bb9c0844309a4cc584bc4fbbdda244b1
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

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