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Triethylamine → (R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinocarbonylbenzamide

HRID 2187465
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2187465
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=2)=[O:8])[CH2:3][CH2:2]1.[NH2:18][C@@H:19]1[CH2:28][CH2:27][C:26]2[C:21](=[C:22]([N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)[CH:23]=[CH:24][CH:25]=2)[CH2:20]1.C(N(CC)CC)C>S(Cl)(Cl)=O.C(Cl)Cl>[CH3:35][N:32]1[CH2:33][CH2:34][N:29]([C:22]2[CH:23]=[CH:24][CH:25]=[C:26]3[C:21]=2[CH2:20][C@H:19]([NH:18][C:13](=[O:15])[C:12]2[CH:11]=[CH:10][C:9]([C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[O:8])=[CH:17][CH:16]=2)[CH2:28][CH2:27]3)[CH2:30][CH2:31]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 47142364-(Morpholine-4-carbonyl)benzoic acidHCID 53960413(R)-2-amino-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydronaphthalene

Produkt 1

HCID 54251823(R)-N-[8-(4-Methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinocarbonylbenzamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344
Dichloromethane
Lösungsmittel
HCID 24386Thionyl ChlorideLösungsmittel

Versuchsvorschrift

4-Morpholinocarbonylbenzoic acid (130 mg, 0.54 mmol; described in: J. Med Chem. 1994, 37(26), 4538-4554) was dissolved in thionyl chloride (5 mL). When the acid was dissolved, the excess of thionyl chloride was evaporated in vacuo, the residue was treated with toluene and again the solvent was removed in vacuo. The crude acid chloride was dissolved in methylene chloride (5 mL) and added dropwise to an ice-cooled solution of (R)-2-amino-8-(4-methylpiperazine-1-yl)-1,2,3,4-tetrahydronaphthalene (120 mg, 0.49 mmol) and triethylamine (100 μL, 0.73 mmol) in methylene chloride (20 mL). After the addition, the reaction was allowed to stir at ambient temperature for 15 min and was then washed with dilute aqueous sodium hydrogen carbonate. The phases were separated and the organic phase was dried (Na2SO4), filtered and evaporated in vacuo to give a crude product which was purified on a silica gel column using using chloroform/methanol/concentrated ammonium hydroxide (95:4:0.5) as the eluent. Yield: 160 mg (72%) of the title compound as white crystals: mp 124-127° C.; [α]21D −40° (c 1.0, chloroform); EIMS (70 eV) m/z (relative intensity) 462 (2, M+).

Aufarbeitung

  1. dissolutionWhen the acid was dissolved
  2. customthe excess of thionyl chloride was evaporated in vacuo
  3. additionthe residue was treated with toluene
  4. customagain the solvent was removed in vacuo
  5. dissolutionThe crude acid chloride was dissolved in methylene chloride (5 mL)
  6. additionadded dropwise to an ice-
  7. additionAfter the addition
  8. washwas then washed with dilute aqueous sodium hydrogen carbonate
  9. customThe phases were separated
  10. dry with materialthe organic phase was dried (Na2SO4)
  11. filtrationfiltered
  12. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bb258f91bd1d454fa4b028922aff91fa
Quelldatensatz
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06410530B1

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