Morpholine → N-[8-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoyl]morpholine

HRID 2268446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2268446
[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](O)=[O:31])[CH2:14][C:13]2[C:8](=[C:9]([O:21][CH3:22])[C:10]([O:19][CH3:20])=[C:11]([O:17][CH3:18])[C:12]=2[O:15][CH3:16])[CH2:7]1)=[O:5])[CH3:2].[NH:33]1[CH2:38][CH2:37][O:36][CH2:35][CH2:34]1.Cl.C(N=C=NCCCN(C)C)C.O.ON1C2C=CC=CC=2N=N1>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1([CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([N:33]2[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)=[O:31])[CH2:7][C:8]2[C:13](=[C:12]([O:15][CH3:16])[C:11]([O:17][CH3:18])=[C:10]([O:19][CH3:20])[C:9]=2[O:21][CH3:22])[CH2:14]1)=[O:5])[CH3:2]

Komponenten

6

Edukt 4

HCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 183486378-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid

Produkt 1

HCID 18348513N-[8-(2-Ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoyl]morpholineAusbeute 93,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A THF (4.0 ml) suspension of 8-(2-ethoxycarbonyl-4,5,6,7-tetramethoxyindan-2-yl)octanoic acid (114 mg, 0.252 mmols), morpholine (0.110 ml, 1.26 mmols), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (96.6 mg, 0.504 mmols) and 1-hydroxybenzotriazole monohydrate (77.2 mg, 0.504 mmols) was stirred at room temperature for 12 hours. The reaction mixture was concentrated in vacuo, to which was added water. Then, this was extracted with ethyl acetate, and the organic layer was washed with water and a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out, and the resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1) to obtain the entitled compound (123 mg) as an oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo, to which
  2. additionwas added water
  3. extractionThen, this was extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materiala saturated aqueous sodium chloride solution, and then dried
  6. customThe solvent was evaporated out
  7. customthe resulting crude product was purified by silica gel column chromatography (hexane:ethyl acetate=4:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-fb77886e38dc4c1b901b16b38b7d8bc8
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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