Potassium Carbonate → Buspirone

HRID 1649475

Reaktionsgleichung

Reaktionsgleichung von HRID 1649475
[CH2:1]1[CH2:5][C:4]2([CH2:12][C:10](=[O:11])[NH:9][C:7](=[O:8])[CH2:6]2)[CH2:3][CH2:2]1.[Br-].[N:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH2:29][CH2:28][N+:23]2([CH2:27][CH2:26][CH2:25][CH2:24]2)[CH2:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+]>C(O)CCC>[N:14]1[CH:19]=[CH:18][CH:17]=[N:16][C:15]=1[N:20]1[CH2:29][CH2:28][N:23]([CH2:24][CH2:25][CH2:26][CH2:27][N:9]2[C:7](=[O:8])[CH2:6][C:4]3([CH2:5][CH2:1][CH2:2][CH2:3]3)[CH2:12][C:10]2=[O:11])[CH2:22][CH2:21]1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 1368438-Azaspiro(4.5)decane-7,9-dioneHCID 6575058-Aza-5-azoniaspiro(4.5)decane, 8-(2-pyrimidinyl)-, bromide (1:1)

Produkt 1

HCID 2477BuspironeAusbeute 66,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A mixture of 3,3-tetramethyleneglutarimide (7.5 g., 0.045 mole), 8-(2-pyrimidinyl)-8-aza-5-azoniaspiro[4.5]decane bromide (15.4 g., 0.045 mole), potassium carbonate (6.2 g., 0.045 mole) in 250 ml. of n-butanol is refluxed for a 21 hour period, filtered and evaporated to dryness. Residual material is warmed 45 minutes with acetic anhydride and evaporated to dryness. Water is added to the residue and the mixture basified with aqueous sodium hydroxide. Insolubles are collected and washed with water to provide 11.5 g. (66.5% yield) of 8-[4-[4-(2-pyrimidinyl)-1-piperazinyl]-butyl]-8-azaspiro[4.5]decane-7,9-dione as the free base, m.p. 90°-98° C.

Aufarbeitung

  1. filtrationfiltered
  2. customevaporated to dryness
  3. temperatureResidual material is warmed 45 minutes with acetic anhydride
  4. customevaporated to dryness
  5. additionWater is added to the residue
  6. customInsolubles are collected
  7. washwashed with water
  8. customto provide 11.5 g

Quellen und Nachweise

ORD-Eintrag
ord-0a28acf637e04c94b8a767ecb5058847
Quelldatensatz
uspto-grants-1983_11
Patentnummer
US04417049

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