Hydrochloric Acid → HCID 12988961, 화합물

HRID 2220089노트

반응식

HRID 2220089 반응식
[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]

참가 물질

9

반응물 4

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

생성물 1

HCID 12988961HCID 12988961, 화합물

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0d09bf24764b4814b6afff112e6b4454
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417043B2

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