Hydrofluoric Acid → 8-chloro-6,11-dihydro-11-(1-methyl-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

HRID 569209Notes

Reaction equation

HRID 569209 reaction equation
Cl.CN1[CH2:8][CH2:7][CH:6]([C:9]([C:11]2[C:16]([CH2:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)=[CH:15][CH:14]=[CH:13][N:12]=2)=O)CC1.F.[B].C1N[C:33](=O)[NH:32][C:30](=O)[C:29]=1C(F)(F)F>>[Cl:25][C:21]1[CH:22]=[CH:23][C:24]2[C:9](=[C:6]3[CH2:7][CH2:8][CH2:29][CH2:30][N:32]3[CH3:33])[C:11]3=[N:12][CH:13]=[CH:14][CH:15]=[C:16]3[CH2:17][CH2:18][C:19]=2[CH:20]=1

Participants

4

Reactant 3

HCID 14917Hydrofluoric AcidHCID 13920590(3-(2-(3-Chlorophenyl)ethyl)-2-pyridinyl)(1-methyl-4-piperidinyl)methanone hydrochlorideHCID 86742042Boron trifluoridine

Product 1

HCID 543724358-chloro-6,11-dihydro-11-(1-methyl-piperidylidene)-5H-benzo[5,6]cyclohepta[1,2-b]pyridine

Procedure

To a solution of a product of Step D above (59 g, 0.15 mole) in 120 mL (120 g, 6.0 mole) of hydrofluoric acid at -35° C. is added boron trifluoridine (44.3 g, 0.66 mole) over 1 hour. Completeness of the reaction is determined by thin-layer chromatography. The reaction is quenched using ice, water and potassium hydroxide to a final pH of 10. The product is extracted into toulene and the toluene solution is washed with water and brine. The toluene solution is concentrated to a residue, which is dissolved in hot hexane. Insolubles are removed by filtration and the filtrate is concentrated to an off-white powder. Yield: 45.7 g (HPLC purity 96%), 92% of theory.

Workup

  1. customThe reaction is quenched
  2. extractionThe product is extracted into toulene
  3. washthe toluene solution is washed with water and brine
  4. concentrationThe toluene solution is concentrated to a residue, which
  5. dissolutionis dissolved in hot hexane
  6. customInsolubles are removed by filtration
  7. concentrationthe filtrate is concentrated to an off-white powder

Sources & evidence

ORD record
ord-1afaa05cf2ea4ccd8fbba6b21f96aebb
Source dataset
uspto-grants-1988_03
Patent number
US04731447

Reaction notes

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