Potassium Carbonate → HCID 22313744, compound

HRID 965922Notes

Reaction equation

HRID 965922 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]2[CH2:13][CH2:12][NH:11][CH2:10]2)=[CH:4][CH:3]=1.[O:14]1[CH2:16][CH:15]1[CH2:17][O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[NH:25][C:26](=[O:28])[CH3:27].C([O-])([O-])=O.[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][CH:9]2[CH2:13][CH2:12][N:11]([CH2:16][CH:15]([OH:14])[CH2:17][O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[NH:25][C:26](=[O:28])[CH3:27])[CH2:10]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2796251N-[2-(oxiran-2-ylmethoxy)phenyl]acetamideHCID 13606208HCID 13606208, compound

Product 1

HCID 22313744HCID 22313744, compoundYield 39.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of N-(4-chlorophenyl)-3-pyrrolidinamine (2×CF3COOH), (186 mg, 0.438 mmol), N-[2-(2-oxiranylmethoxy)phenyl]acetamide (91 mg, 0.438 mmol) and K2CO3 (200 mg) in ethanol (6 mL) was kept on stirring at 65° C. for 2.5 h. The volatiles were removed in vacuo. The residue was partitioned between ethyl acetate and aq. NH4Cl solution. The organic layer was washed with water, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (0-3% MeOH in CHCl3) to give the titled product (70 mg).

Workup

  1. customThe volatiles were removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and aq. NH4Cl solution
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (0-3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-514caea028ff42869ce9ea69b123a1ca
Source dataset
uspto-grants-2005_10
Patent number
US06951874B2

Reaction notes

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