Diiodomethane → 4-Phenyl-4-[(1-(3,5-bis(trifluoromethyl)phenyl)cyclopropyloxy)methyl]piperidine Hydrochloride

HRID 962486

반응식

HRID 962486 반응식
[ClH:1].[C:2]1([C:8]2([CH2:14][O:15][CH:16]([C:19]3[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:29]([F:32])([F:31])[F:30])[CH:20]=3)[CH2:17]O)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:33]([Zn]CC)C.ICI>CCOCC.C(OCC)(=O)C.Cl.CCOCC>[ClH:1].[C:2]1([C:8]2([CH2:14][O:15][C:16]3([C:19]4[CH:20]=[C:21]([C:29]([F:31])([F:30])[F:32])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=4)[CH2:17][CH2:33]3)[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 6346DiiodomethaneHCID 190847004-Phenyl-4-((1-(3,5-bis(trifluoromethyl)phenyl)-2-hydroxyethoxy) methyl)piperidine HydrochlorideHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 190846904-Phenyl-4-[(1-(3,5-bis(trifluoromethyl)phenyl)cyclopropyloxy)methyl]piperidine Hydrochloride

시약·촉매·용매 3

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매HCID 10953452Ether hydrochloride용매

반응 조건

온도
0 °C

실험 절차

The compound of Example 1 (c) (0.500 g, 0.922 mmol) was dissolved in anhydrous ether (10 ml) and diethylzinc (1.0M solution in hexanes, 1.84 ml, 1.84 mmol) was added. The solution was cooled to 0° C. and diiodomethane (0.15 ml 1.84 mmol) was added. The reaction was diluted with ethyl acetate (50 ml) and washed with saturated aqueous ammonium chloride solution. The organic layer was dried over (MgSO4) and evaporated. The residue was purified by chromatography on silica eluting with 5% ethyl acetate/hexanes→10% ethyl acetate/hexanes. The product obtained was left standing in HCl/ether for 16 h. The solvent was removed in vacuo and the title compound suspended in ether and filtered. 1H NMR (DMSO-d6) δ 7.90 (1H, s), 7.50 (2H, s), 7.29-7.40 (5H, m), 3.36 (2H, s), 3.17 (2H, m), 2.74 (2H, m), 2.30 (2H, m), 2.01 (2H, m), 1.13 (4H, m). MS (Cl+) 444 [M+H]+.

후처리

  1. washwashed with saturated aqueous ammonium chloride solution
  2. dry with materialThe organic layer was dried over (MgSO4)
  3. customevaporated
  4. customThe residue was purified by chromatography on silica eluting with 5% ethyl acetate/hexanes
  5. customThe product obtained
  6. waitwas left
  7. customThe solvent was removed in vacuo
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-ae3b656c0c7849aca4223139c73b343d
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05760018

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