Hydrochloric Acid → HCID 12988961, compound

HRID 2220089Notes

Reaction equation

HRID 2220089 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[CH:24]([O:26]CCCC)=[CH2:25].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2].C(Cl)Cl.CCN(CC)CC>[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12]([C:24](=[O:26])[CH3:25])[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8108Butyl vinyl etherHCID 812191,3-Bis(diphenylphosphino)propaneHCID 12988960HCID 12988960, compound

Product 1

HCID 12988961HCID 12988961, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of trifluoro-methanesulfonic acid 3-(1-propyl-piperidin-4-yl)-phenyl ester (300 mg) in DMF (4 ml) under argon atm at r.t. was subsequently added NEt3 (356 μL), butyl vinyl ether (823 μL), 1,3-bis(diphenylphosphino)propane (50 mg), and Pd(OAc)2 (19 mg). The reaction mixture was then heated to 80° C. and after 2 h the reaction was stopped. 5% Hydrochloric acid solution (6 ml) was added and the combined mixture stirred for 45 min. Then CH2Cl2 was added and the phases were separated. The aqueous layer was then extracted with CH2Cl2. The combined organic phases were dried (MgSO4), filtered and evaporated to dryness. The crude product was purified by flash chromatography (MeOH:CH2Cl2 (1:9 (v/v)). Collection of the fractions containing pure product and evaporation of the solvent afforded pure 1-[3-(1-Propyl-piperidin-4-yl)-phenyl]-ethanone (35 mg). MS m/z (rel. intensity, 70 eV) 245 (M+, 4), 216 (bp), 100 (19), 70 (36), 57 (13).

Workup

  1. customat r.t.
  2. customthe phases were separated
  3. extractionThe aqueous layer was then extracted with CH2Cl2
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude product was purified by flash chromatography (MeOH:CH2Cl2 (1:9 (v/v))
  8. customCollection of the fractions
  9. additioncontaining pure
  10. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-0d09bf24764b4814b6afff112e6b4454
Source dataset
uspto-grants-2008_08
Patent number
US07417043B2

Reaction notes

Loading…