Trifluoroacetic acid → HCID 22675313、化合物

HRID 1006065

反応式

HRID 1006065 の反応式
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][CH:21]([CH2:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=3[CH:33](O)[CH3:34])[CH2:20][CH2:19]2)[CH:13]=[CH:14][CH:15]=1.C([SiH](CC)CC)C.C(=O)([O-])O.[Na+].COC1C=C(CCN2CCC(CC3C=C(OC)C=CC=3CC)CC2)C=CC=1.C([Si](CC)(CC)O)C.[ClH:83].C(OCC)C>ClCCl.C(OCC)C.C(OCC)(=O)C>[ClH:83].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][CH2:17][N:18]2[CH2:19][CH2:20][CH:21]([CH2:24][C:25]3[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=3[CH2:33][CH3:34])[CH2:22][CH2:23]2)[CH:13]=[CH:14][CH:15]=1

参加物

11

反応物 7

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69005TriethylsilanolHCID 516892Sodium BicarbonateHCID 10953452Ether hydrochlorideHCID 22675304N-(2-(3-methoxyphenyl)ethyl)-4-(2-(1-hydroxyethyl)-5-methoxybenzyl)piperidineHCID 22675314N-(2-(3-methoxyphenyl)ethyl)-4-(2-ethyl-5-methoxybenzyl)piperidine

生成物 1

HCID 22675313HCID 22675313、化合物収率 79.6%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

Trifluoroacetic acid (0.5 ml) was added dropwise to a solution of N-(2-(3-methoxyphenyl)ethyl)-4-(2-(1-hydroxyethyl)-5-methoxybenzyl)piperidine (250 mg, 0.65 mmol) and triethylsilane (91 mg, 0.78 mmol) in dichloromethane (5 ml) under ice-cooling, and the reaction mixture was stirred as it was for 2 hours. Ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added thereto to effect separation, and the organic layer was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a silica gel column chromatography (chloroform/methanol=50/1) to obtain a mixture of N-(2-(3-methoxyphenyl)ethyl)-4-(2-ethyl-5-methoxybenzyl)piperidine and triethylsilanol. This mixture was dissolved in dichloromethane (5 ml), followed by adding thereto a 1N hydrogen chloride-diethyl ether solution (1 ml, 1 mmol), and the solvent was distilled off under reduced pressure. The residue was suspended in diethyl ether and the precipitate was collected by filtration and washed with diethyl ether to obtain the title compound (209 mg, 79%) as white powder.

後処理

  1. temperaturecooling
  2. customseparation
  3. washthe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe residue was purified by a silica gel column chromatography (chloroform/methanol=50/1)
  8. customto obtain
  9. additionby adding
  10. filtrationthe precipitate was collected by filtration
  11. washwashed with diethyl ether

出典と根拠

ORDレコード
ord-32603b56029e4efabf3f59675f734cf0
出典データセット
uspto-grants-2004_09
特許番号
US06787560B2

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