Diisopropylethylamine → 1-[2-(Isochroman-1-yl)ethyl]-4-(2-methylphenyl)piperazine dihydrochloride

HRID 368814

反応式

HRID 368814 の反応式
[Cl:1][CH2:2]CC1C2C(=CC=CC=2)CCO1.O.[ClH:15].Cl.[CH:17]1([CH2:27][CH2:28][N:29]2[CH2:34][CH2:33][N:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3OC)[CH2:31][CH2:30]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][O:18]1.C(N(C(C)C)CC)(C)C>C(O)CO>[ClH:1].[ClH:15].[CH:17]1([CH2:27][CH2:28][N:29]2[CH2:30][CH2:31][N:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=3[CH3:2])[CH2:33][CH2:34]2)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20][CH2:19][O:18]1

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 10607966HCID 10607966、化合物HCID 232889511-[2-(Isochroman-1-yl)ethyl]-4-(2-methoxyphenyl)piperazine dihydrochloride monohydrate

生成物 1

HCID 232887581-[2-(Isochroman-1-yl)ethyl]-4-(2-methylphenyl)piperazine dihydrochloride

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

A mixture of 1-(2-chloroethyl)isochroman (LXIV, PREPARATION 2, 0.2466 g, 1.25 mmol), 1-(2-methylphenyl)piperazine dihydrochloride (XI, 0.5327 g, 2.14 mmol), diisopropylethylamine (0.98 ml, 5.63 mmol) and ethylene glycol (2.5 ml) is stirred under nitrogen at 100° for 3 days. The reaction mixture is cooled and partitioned between aqueous sodium bicarbonate and ethyl acetate. The combined organic phase is washed with saline, dried over magnesium sulfate and concentrated. The residue is chromatographed on silica gel eluting with methanol/dichloromethane (2/98). The appropriate fractions are pooled and concentrated to give the free base of the title compound. The dihydrochloride salt is formed using hydrochloric acid/methanol to give the title compound, mp 207.5-210.5°; MS (m/z) 336; IR (mineral oil) 770, 2406, 2435, 2992, 2364 and 1489 cm-1.

後処理

  1. temperatureThe reaction mixture is cooled
  2. custompartitioned between aqueous sodium bicarbonate and ethyl acetate
  3. washThe combined organic phase is washed with saline
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel eluting with methanol/dichloromethane (2/98)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-45ff07c4c7a34bb9a39e451d8e63eb3f
出典データセット
uspto-grants-2000_10
特許番号
US06133446

関連ノート

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