1-Benzyl-4-piperidone → 1-benzyl-6'-bromo-3',4'-dihydro-spiro[piperidine-4,2'(1H)-quinazoline]-4'-one

HRID 518186

Reaktionsgleichung

Reaktionsgleichung von HRID 518186
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:24]=[CH:23][C:22]([Br:25])=[CH:21][C:17]=1[C:18]([NH2:20])=[O:19].C([O-])(O)=O.[Na+]>OS(O)(=O)=O.C(O)(=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]2([NH:20][C:18](=[O:19])[C:17]3[C:16](=[CH:24][CH:23]=[C:22]([Br:25])[CH:21]=3)[NH:15]2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 192201-Benzyl-4-piperidoneHCID 516892Sodium BicarbonateHCID 50192712-Amino-5-bromobenzamide

Produkt 1

HCID 460779491-benzyl-6'-bromo-3',4'-dihydro-spiro[piperidine-4,2'(1H)-quinazoline]-4'-oneAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1118Sulfuric AcidKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

N-benzyl 4-piperidone (1.76 g, 9.3 mmol) and concentrated H2SO4 (2 drops) were added to a solution of 2-amino-5-bromo-benzamide (2 g, 9.3 mmol) dissolved in acetic acid (15 ml). The mixture was stirred at RT for 2 h, then poured into ice water and brought to a pH value of 8-9 with saturated NaHCO3. The white precipitate was filtered off and washed with water, giving 1-benzyl-6′-bromo-3′,4′-dihydro-spiro[piperidine-4,2′(1′H)-quinazoline]-4′-one (1.05 g).

Aufarbeitung

  1. filtrationThe white precipitate was filtered off
  2. washwashed with water

Quellen und Nachweise

ORD-Eintrag
ord-08b9adbe670d4ae999557ade75361032
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115148B2

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