Boron trifluoride → HCID 21498268, compound

HRID 1730506Notes

Reaction equation

HRID 1730506 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]([CH2:14][C:15]#[CH:16])[C:11](=[O:17])[CH:10]([CH3:18])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B(F)(F)F.ClC(Cl)(Cl)C(O)=[O:26]>CO>[CH2:14]([CH:12]1[C:11](=[O:17])[CH:10]([CH3:18])[CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13]1)[C:15]([CH3:16])=[O:26]

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 6421Trichloroacetic AcidHCID 21498286HCID 21498286, compound

Product 1

HCID 21498268HCID 21498268, compoundYield 63,630.301%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of the crude 1-benzyl-3-methyl-5-prop-2-ynyl-4-piperidone (10 g)from Example 5 in methanol (15 ml) was added dropwise to a stirred mixture of red mercuric oxide (1.5 g), boron trifluoride diethyletherate (1.1 ml),trichloroacetic acid (10 mg) and methanol (5 ml). The resulting mixture wasstirred for 3 hours at room temperature and then filtered and the filtrate evaporated. The residue was treated at 50° C for 1 hour with 10% sulphuric acid (100 ml), the mixture filtered and the filtrate basified with sodium carbonate. Extraction with ether, drying of the extract with magnesium sulphate and evaporation gave 10.1 g of the crude title compound(about 75% by g.l.c.) as a brown oil.

Workup

  1. filtrationfiltered
  2. customthe filtrate evaporated
  3. additionThe residue was treated at 50° C for 1 hour with 10% sulphuric acid (100 ml)
  4. filtrationthe mixture filtered
  5. extractionExtraction with ether
  6. customdrying of the
  7. extractionextract with magnesium sulphate and evaporation

Sources & evidence

ORD record
ord-6278ce37b938416b8928d58e9a30ff68
Source dataset
uspto-grants-1976_11
Patent number
US03992544

Reaction notes

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