2-Bromopropane → 4-(Methoxymethyl)-N-phenyl-1-(propan-2-yl)piperidin-4-amine

HRID 28162Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 28162
Br[CH:2]([CH3:4])[CH3:3].[CH3:5][O:6][CH2:7][C:8]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C>CN(C)C(=O)C>[CH3:5][O:6][CH2:7][C:8]1([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:13][CH2:12][N:11]([CH:2]([CH3:4])[CH3:3])[CH2:10][CH2:9]1

Komponenten

5

Edukt 3

HCID 63582-BromopropaneHCID 8471TriethylamineHCID 183199324-(Methoxymethyl)-N-phenylpiperidin-4-amine

Produkt 1

HCID 233390404-(Methoxymethyl)-N-phenyl-1-(propan-2-yl)piperidin-4-amineAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

A mixture of 10 parts of 2-bromopropane, 9 parts of 4-(methoxymethyl)-N-phenyl-4-piperidinamine, 4.9 parts of N,N-diethylethanamine and 72 parts of N,N-dimethylacetamide is stirred and refluxed for 10.25 hours. After cooling, the formed N,N-diethylethanamine hydrobromide is filtered off and the filtrate is diluted with water. The product is extracted with methylbenzene. The extract is washed thoroughly with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (90:10) as eluent. The pure fractions are collected and the eluent is evaporated, yielding 5.7 parts (42.6%) of 4-(methoxymethyl)-1-(1-methylethyl)-N-phenyl-4-piperidinamine as an oily residue.

Aufarbeitung

  1. temperaturerefluxed for 10.25 hours
  2. temperatureAfter cooling
  3. filtrationthe formed N,N-diethylethanamine hydrobromide is filtered off
  4. additionthe filtrate is diluted with water
  5. extractionThe product is extracted with methylbenzene
  6. washThe extract is washed thoroughly with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue is purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (90:10) as eluent
  12. customThe pure fractions are collected
  13. customthe eluent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b65bd2258c17427493342d94443c8432
Quelldatensatz
uspto-grants-1980_09
Patentnummer
US04225606

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