Potassium Carbonate → HCID 20638934, compound

HRID 565675Notes

Reaction equation

HRID 565675 reaction equation
CS(O[CH2:6][C@:7]1([CH3:19])[CH2:11][C:10]2[C:12]([CH3:18])=[CH:13][C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1)(=O)=O.[C:20]1([CH:26]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[NH:27][CH:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C.O>[CH3:19][C@@:7]1([CH2:6][N:31]2[CH2:32][CH2:33][CH:28]([NH:27][CH:26]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:29][CH2:30]2)[CH2:11][C:10]2[C:12]([CH3:18])=[CH:13][C:14]([CH3:17])=[C:15]([CH3:16])[C:9]=2[O:8]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 13644890HCID 13644890, compoundHCID 86756224HCID 86756224, compound

Product 1

HCID 20638934HCID 20638934, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
177 °C

Procedure

A suspension of (S)-(2,3-dihydro-2,4,6,7-tetramethylbenzofuran-2-yl)methyl methanesulfonate (0.34 g), N-(diphenylmethyl)-4-piperidinamine (0.73 g), and potassium carbonate (0.38 g) in N,N-dimethylacetamide (2 mL) was stirred under argon gas at 177° C. for 6 hours. This reaction mixture was diluted with water and extracted with diisopropyl ether. The organic layer was washed with water and extracted with 1N-hydrochloric acid. The aqueous layer was made basic with 2N-sodium hydroxide/water and extracted with diisopropyl ether. The extract was washed with water and saturated aqueous sodium chloride solution, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3) to provide the title compound (0.49 g). Yield 79%.

Workup

  1. extractionextracted with diisopropyl ether
  2. washThe organic layer was washed with water
  3. extractionextracted with 1N-hydrochloric acid
  4. extractionextracted with diisopropyl ether
  5. washThe extract was washed with water and saturated aqueous sodium chloride solution
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-99c95f5426d64c42a4fc1658333c567a
Source dataset
uspto-grants-2001_01
Patent number
US06172085B2

Reaction notes

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