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

HRID 962486

反応式

HRID 962486 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒HCID 10953452Ether hydrochloride溶媒

反応条件

温度
0 °C

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-ae3b656c0c7849aca4223139c73b343d
出典データセット
uspto-grants-1998_06
特許番号
US05760018

関連ノート

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