Triethylamine → HCID 9794842, compound

HRID 323770Notes

Reaction equation

HRID 323770 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C@H:10]3[CH2:12][C@H:11]3NC)[C:4]=2[CH2:3][CH2:2]1.[CH2:15]([N:17](CC)CC)C.[C:22](Cl)(=[O:25])[CH2:23][CH3:24]>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C@H:10]3[CH2:12][C@H:11]3[CH2:15][NH:17][C:22](=[O:25])[CH2:23][CH3:24])[C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 54474819HCID 54474819, compound

Product 1

HCID 9794842HCID 9794842, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (cis)-2-(2,3-dihydrobenzofuran-4-yl)cycloprop-1-yl methyl amine (0.43 mmol), triethylamine (1.30 mmol) and propionyl chloride (0.65 mmol) in 10 mL of methylene chloride was stirred at room temperature overnight. The reaction mixture was washed with brine (2×20 mL). The organic phase was separated, dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography (Hex:EtOAc, 4:1) provided 23 mg of the desired product (22%) as a yellow oil. HPLC purity >95%.

Workup

  1. washThe reaction mixture was washed with brine (2×20 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (Hex:EtOAc, 4:1)

Sources & evidence

ORD record
ord-4fd23fe744c548258c16bdc2385f7b7e
Source dataset
uspto-grants-2001_04
Patent number
US06214869B1

Reaction notes

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