Water → 1-(3-Butynyl)-4-(4-chlorophenyl)piperidine

HRID 1279363

Reaktionsgleichung

Reaktionsgleichung von HRID 1279363
[C:1]([O-])(O)=O.[Na+].[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]2CCNCC2)=[CH:9][CH:8]=1.[C:20]([C:24]1C=C(C=CC=1C)S([O-])(=O)=O)#[C:21]CC.O.[CH3:36][N:37]([CH3:40])[CH:38]=O>>[CH2:36]([N:37]1[CH2:40][CH2:14][CH:13]([C:10]2[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=2)[CH2:1][CH2:38]1)[CH2:24][C:20]#[CH:21]

Komponenten

6

Edukt 5

HCID 962WaterHCID 6228Dimethylformamide2×HCID 516892Sodium BicarbonateHCID 37327804-(4-Chlorobenzyl)piperidineHCID 184280043-Butynyltosylate

Produkt 1

HCID 184279681-(3-Butynyl)-4-(4-chlorophenyl)piperidine

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of NaHCO3(4 g) and 4-[(4-chlorophenyl)methyl]piperidine (18 mmol) in dimethylformamide (DMF) (25 mL) is stirred under a N2 atm at 0° C., and treated dropwise with 3-butynyltosylate (20 mmol) as a solution in DMF (50 mL). The reaction mixture is heated at 80° C. and stirred an additional 18 hours. After cooling the reaction mixture is stirred vigorously with the addition of water (200 mL), and then extracted with ethyl acetate. The organic layer is dried over magnesium sulfate, filtered and evaporated. The residue is purified by silica gel column chromatography (100:1 CH2Cl2:MeOH) to give 1-(3-butynyl)-4-(4-chlorophenyl)piperidine.

Aufarbeitung

  1. temperatureThe reaction mixture is heated at 80° C.
  2. stirringstirred an additional 18 hours
  3. temperatureAfter cooling the reaction mixture
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by silica gel column chromatography (100:1 CH2Cl2:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-55c4a930c8b8476698b4f36da2dadb3c
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06448270B1

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