Sodium hydride → 1-Cyclopropylmethyl-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromide

HRID 867677Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 867677
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][N:11]=2)[CH2:6][CH2:5]1.Cl[CH2:20][CH:21]1[CH2:23][CH2:22]1.[BrH:24].CCOCC>CN(C)C=O.CCOCC>[BrH:24].[CH:21]1([CH2:20][N:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:10]([CH:7]3[CH2:6][CH2:5][N:4]([CH3:3])[CH2:9][CH2:8]3)=[N:11]2)[CH2:23][CH2:22]1

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 80013(Chloromethyl)cyclopropaneHCID 86739792Ether hydrobromideHCID 178480237HCID 178480237, Verbindung

Produkt 1

HCID 140325091-Cyclopropylmethyl-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromideAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a stirred mixture of 1.19 g of sodium hydride (50% oil dispersion) in 65 ml of dimethylformamide was added, dropwise, 4.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 20 ml of hot dimethylformamide. The mixture was stirred for 1 hr at ambient temperature and then 1.40 g of chloromethylcyclopropane in 10 ml of dimethylformamide was added dropwise. The reaction mixture was stirred for 21/2 days at ambient temperature. The reaction mixture was quenched with water, extracted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to yield an oil. The oil was dissolved in ether and saturated hydrogen bromide/ether solution was added dropwise to precipitate a salt. The salt was recrystallized from toluene and ethyl acetate to yield 2.8 g (32%) of product, mp 177°-179° C.

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 21/2 days at ambient temperature
  3. customThe reaction mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed in vacuo
  8. customto yield an oil
  9. customto precipitate a salt
  10. customThe salt was recrystallized from toluene and ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-ff730bccbf7b472ba00f423acf0448fe
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04775761

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