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Hydrochloric Acid → Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMate

HRID 340420
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 340420
[CH3:1][O-:2].[Na+].Br[N:5]1[C:9](=[O:10])CCC1=O.[CH3:12][N:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:27]=[C:26]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])[C:22](C(N)=O)=[CH:21][N:20]=2)[CH2:15][CH2:14]1.Cl>CO.ClCCl>[CH3:1][O:2][C:9](=[O:10])[NH:5][C:22]1[CH:21]=[N:20][C:19]([N:16]2[CH2:15][CH2:14][N:13]([CH3:12])[CH2:18][CH2:17]2)=[CH:27][C:26]=1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[CH3:34]
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Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 114837284-(2-Methylphenyl)-6-(4-methyl-1-piperazinyl)-3-pyridinecarboxamide

Produkt 1

HCID 12167320Methyl (6-(4-Methylpiperazin-1-yl)-4-(o-tolyl)pyridin-3-yl)carbaMateAusbeute 102,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×
HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

2.15 ml (11.6 mMol) Sodium methoxide in methanol were added over 30 minutes to a suspension of 0.85 g (4.6 mMol) N-bromosuccinimide in 5.0 ml dichloromethane cooled to −5° C. The reaction mixture was stirred 16 hours at −5° C. Still at this temperature, a solution of 1.0 g (3.1 mMol) 6-(4-methyl-piperazin-1-yl)-4-o-tolyl-nicotinamide in 5.0 ml methanol was added over 20 minutes and stirred for 5 hours. 7.1 ml (7.1 mMol) Aqueous HCl 1N and 20 ml dichloromethane were added. The phases were separated and the organic phase was washed with deionized water. The aqueous phases were extracted with dichloromethane, brought to pH=8 with aqueous NaOH 1N and further extracted with dichloromethane. The latter organic, extracts were combined, dried (Na2SO4) and concentrated to yield 1.08 g (quant.) [6-(4-methyl-piperazin-1yl)-4-o-tolyl-pyridin-3-yl]-carbamic acid methyl ester as a grey foam. MS (ISP): 341 (M+H+, 100), 284 (35).

Aufarbeitung

  1. stirringstirred for 5 hours
  2. customThe phases were separated
  3. washthe organic phase was washed with deionized water
  4. extractionThe aqueous phases were extracted with dichloromethane
  5. extractionfurther extracted with dichloromethane
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-dfd27b17e5dd4bd89f95215e61192b2e
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08895586B2

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