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Dimethylcarbamoyl Chloride → 1-(6-Dimethylaminocarbonylaminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine

HRID 351758
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 351758
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:32][N:33]([CH3:37])[C:34](Cl)=[O:35]>C1COCC1>[CH3:32][N:33]([CH3:37])[C:34]([NH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=3)[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)=[O:35]
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Komponenten

5

Edukt 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 235048071-(6-Aminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine2×

Produkt 1

HCID 235047741-(6-Dimethylaminocarbonylaminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel
2×

Versuchsvorschrift

1-(6-Aminoindan-1-ylmethyl)-4-(4-fluorophenyl)piperidine, 2a (3 g) was dissolved in THF (50 ml) and triethylamine (2 g) was added. At 5° C. dimethylcarbamoylchloride (1 g) in THF (15 ml) was added dropwise. After completed addition the mixture was refluxed for 1.5 hours. THF was evaporated. Water was added and extraction with dichloromethane (2×50 ml) and work-up as above of the combined organic phases yielded crude title product, which was purified by column chromatography on silica gel (eluted with 4% triethylamine in a 1:1 mixture of ethyl acetate and heptane). The pure title compound 6a crystallized from diethyl ether. Yield: 1.4 g, mp: 141-144° C. 1H NMR (CDCl3): 81.65-2.55 (m, 10H); 2.70 (dd, 1H); 2.70-2.95 (m, 2H); 2.95-3.05 (m, 1H); 3.05 (s, 6H); 3.15 (broad d, 1H); 3.35 (qui, 1H); 6.25 (s, 1H); 6.95-7.25 (m, 6H); 7.45 (s, 1H).

Aufarbeitung

  1. additionaddition the mixture
  2. temperaturewas refluxed for 1.5 hours
  3. customTHF was evaporated
  4. additionWater was added
  5. extractionextraction with dichloromethane (2×50 ml)

Quellen und Nachweise

ORD-Eintrag
ord-4e893f8437504c049054d5184d3b0630
Quelldatensatz
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06743808B1

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