4-(Bromomethyl)benzoic acid → 4-((1-Methylspiro[indolin-3,4'-piperidin]-1'-yl)methyl)benzoic acid

HRID 1615454Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1615454
[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]2([CH2:9][CH2:8][NH:7][CH2:6][CH2:5]2)[CH2:3]1.Br[CH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=1.C(N(CC)C(C)C)(C)C>C(O)C>[CH3:1][N:2]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4]2([CH2:5][CH2:6][N:7]([CH2:17][C:18]3[CH:26]=[CH:25][C:21]([C:22]([OH:24])=[O:23])=[CH:20][CH:19]=3)[CH2:8][CH2:9]2)[CH2:3]1

Komponenten

5

Edukt 3

HCID 225994-(Bromomethyl)benzoic acidHCID 81531Diisopropylethylamine2×HCID 106557391-Methyl-1,2-dihydrospiro[indole-3,4'-piperidine]

Produkt 1

HCID 709268554-((1-Methylspiro[indolin-3,4'-piperidin]-1'-yl)methyl)benzoic acidAusbeute 142,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixed solution of 1-methylspiro[indolin-3,4′-piperidine] (1.0 g) synthesized according to a method described in [WO 2011/046851 pamphlet, (preparation 15)], 4-(bromomethyl) benzoic acid (1.08 g), and N,N-diisopropylethylamine (2.61 mL) in ethanol (20 mL) was heated and refluxed for 2 hours. To the resultant reaction mixture, N,N-diisopropylethylamine (1.04 mL) was further added, and the resultant reaction mixture was heated and refluxed for 2 hours. The reaction solution was left to reach room temperature, and from the reaction solution, the solvent was distilled off under reduced pressure to obtain a mixture (2.37 g) containing the subject compound. The resultant mixture was used in the next reaction without further purification.

Aufarbeitung

  1. temperaturewas heated
  2. temperaturerefluxed for 2 hours
  3. additionwas further added
  4. customthe resultant reaction mixture
  5. temperaturewas heated
  6. temperaturerefluxed for 2 hours
  7. waitThe reaction solution was left
  8. customto reach room temperature
  9. distillationfrom the reaction solution, the solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-815190e7562f4d54a7d9f397bea7d3b0
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765752B2

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