Triethylamine → HCID 22595087, compound

HRID 1761279Notes

Reaction equation

HRID 1761279 reaction equation
[NH2:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:26])[CH2:24][CH3:25]>ClCCl.C(OCC)(=O)C>[C:23]([NH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:15])[C:6]=2[CH:5]=[CH:4][CH:3]=1)(=[O:26])[CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 20267Fluoren-9-one, 4-amino-HCID 62324Propionyl chloride

Product 1

HCID 22595087HCID 22595087, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 4-amino-9-fluorenone (0.20 g, 1.0 mmol) in dichloromethane (40 ml) was added triethylamine (0.5 ml, 3.5 mmol), followed by propionyl chloride (0.5 ml, 5.8 mmol). After 20 min the mixture was diluted with ethyl acetate (150 ml) and washed with 2N HCl (100 ml) followed by saturated sodium carbonate (100 ml). The organic phase was separated, dried (MgSO4) and the solvent removed in vacuao. The residue was purified by flash chromatography (silica, heptane:ethyl acetate 7:3) to give 164 mg (63%) of the desired material as a yellow oil.

Workup

  1. washwashed with 2N HCl (100 ml)
  2. customThe organic phase was separated
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuao
  5. customThe residue was purified by flash chromatography (silica, heptane:ethyl acetate 7:3)

Sources & evidence

ORD record
ord-b6b5d4d167e542899f4d7b20d1428d24
Source dataset
uspto-grants-2005_01
Patent number
US06846953B1

Reaction notes

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