Hydrochloric Acid → 2-(4-Ethoxyphenyl)-n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)acetamide

HRID 929737

Reaktionsgleichung

Reaktionsgleichung von HRID 929737
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][NH:7][CH:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27](Cl)=[O:28])=[CH:22][CH:21]=1)[CH3:18].Cl.CCCCCCC>ClCCl>[CH2:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][C:27]([N:7]([CH2:6][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:16][CH:15]=2)[CH:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[O:28])=[CH:22][CH:21]=1)[CH3:18]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 8900HeptaneHCID 28466454-(4-Fluorobenzylamino)-1-methylpiperidineHCID 116297822-(4-ethoxyphenyl)acetyl Chloride

Produkt 1

HCID 102934182-(4-Ethoxyphenyl)-n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

50ELH4 (0.11 g, 0.49 mmol, 1.0 eq.) was transferred to a 4 ml vial and dissolved in dichloromethane. 63ELH19 (0.089 mg, 1.0 eq.) was added and the vial was sealed and the reaction shaken for 20 h. The product was extracted in distilled water (made basic with potassium carbonate, pH 10) and dichloromethane. Dried with sodium sulfate and concentrated. Purified by HPLC. The extraction, drying and concentration was repeated and the product dissolved in dichloromethane (1 ml) and HCl (1 eq., 2 M in ether) is added. This mixture was added drop-wise to an excess of heptane whereupon the salt precipitated. Yield 31.1 mg (16%), UV/MS: 94/100 (M+ 385), tr (A, MS) 2.573.

Aufarbeitung

  1. customthe vial was sealed
  2. extractionThe product was extracted in distilled water (made basic with potassium carbonate, pH 10)
  3. dry with materialDried with sodium sulfate
  4. concentrationconcentrated
  5. customPurified by HPLC
  6. extractionThe extraction
  7. customdrying
  8. concentrationconcentration
  9. dissolutionthe product dissolved in dichloromethane (1 ml)
  10. customprecipitated

Quellen und Nachweise

ORD-Eintrag
ord-d75d849d8c904d44bf24d92fa1a25bba
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296694B2

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