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

HRID 1417795

Reaktionsgleichung

Reaktionsgleichung von HRID 1417795
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-dffdeaf7ad5842958956bc5adc5432f8
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05877317

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