Phenethyl bromide → 1-(2-Phenylethyl)-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromide

HRID 652136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 652136
[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.[Br:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.Br.CCOCC>CN(C)C=O.CCOCC.O>[BrH:19].[C:22]1([CH2:21][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)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

8

Edukt 4

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 86739792Ether hydrobromideHCID 178480237HCID 178480237, Verbindung

Produkt 1

HCID 140325111-(2-Phenylethyl)-3-(1-methyl-4-piperidinyl)-1H-indazole hydrobromideAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel3×

Versuchsvorschrift

To a stirred mixture of 0.86 g of sodium hydride (50% oil dispersion) in 50 ml of dimethylformamide was added, dropwise, 3.0 g of 3-(1-methyl-4-piperidinyl)-1H-indazole in 15 ml of hot dimethylformamide. The reaction mixture was stirred at ambient temperature for 1 hr and then a solution of 3.33 g of (2-bromoethyl)benzene in 10 ml of dimethylformamide was added dropwise. The reaction mixture was stirred for 21/2 days at ambient temperature, cooled to 0°, and water was added dropwise. The mixture was 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 a saturated hydrogen bromide/ether solution was added dropwise. The resultant solid was recrystallized two times from ethanol to yield 2.0 g (36%) of product, mp 163°-164° C.

Aufarbeitung

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 21/2 days at ambient temperature
  3. temperaturecooled to 0°
  4. extractionThe mixture was extracted 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. customThe resultant solid was recrystallized two times from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-21f347a238924514af23d85af2ba5572
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670447

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