Hydrochloric Acid → n,n,-Diethyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzamide

HRID 1371028Notes

Reaction equation

HRID 1371028 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:19])[CH2:9][C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21].O=C1N(P(Cl)(N2CCOC2=O)=O)CCO1.Cl>ClCCl.C(N(CC)CC)C>[CH2:20]([N:22]([CH2:23][CH3:24])[C:14](=[O:16])[C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:19])=[CH:18][CH:17]=1)[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8021DiethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 185102554-[2-(4-Fluorophenyl)-2-oxoethyl]benzoic acid

Product 1

HCID 18510224n,n,-Diethyl-4-[2-(4-fluorophenyl)-2-oxoethyl]benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[2-(4-fluorophenyl)-2-oxoethyl]benzoic acid (0.560 g, 2.17 mmol, Example 3, Step 1), triethylamine (0.620 ml), and diethylamine (0.230 ml) in dichloromethane (5 ml) at room temperature was added bis(2-oxo-3-oxazolidinyl)-phosphinic chloride (0.560 g). After 3 hours, HCl 1M (10 ml) was added and the product was extracted with dichloromethane (10 ml). The organic phase was washed with brine, dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography using hexane/ethyl acetate 50% giving 0.44 g of the title compound.

Workup

  1. extractionthe product was extracted with dichloromethane (10 ml)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-a329ada4a5984dfd8dc9c5c3a8ccabc6
Source dataset
uspto-grants-2003_06
Patent number
US06583126B2

Reaction notes

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