Dimethylformamide → 1-acetyl-N-(2-benzothiazolyl)-N-methyl-4-piperidinemethanamine

HRID 1789495Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1789495
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][NH:11][C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].[CH3:23]N(C)C=O.IC>O>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][N:11]([C:12]2[S:13][C:14]3[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=3[N:16]=2)[CH3:23])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 140489441-acetyl-N-(2-benzothiazolyl)-4-piperidinemethanamine

Produkt 1

HCID 212415871-acetyl-N-(2-benzothiazolyl)-N-methyl-4-piperidinemethanamineAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 8.7 parts of 1-acetyl-N-(2-benzothiazolyl)-4-piperidinemethanamine, 1.44 parts of a sodium hydride dispersion 60% and 270 parts of N,N-dimethylformamide was stirred for 1 hour at room temperature. 5.48 Parts of iodomethane were added dropwise slowly. Upon completion, stirring was continued overnight at room temperature. The reaction mixture was poured into water. The product was extracted with 4-methyl-2-pentanone. The extract was dried, filtered and evaporated in vacuo. The residue was purified by column chromatography (HPLC) over silica gel using a mixture of dichloromethane and methanol (98.75:1.25 by volume) as eluent. The second faction was collected and the eluent was evaporated, yielding 7.6 parts (84%) of 1-acetyl-N-(2-benzothiazolyl)-N-methyl-4-piperidinemethanamine as a residue (intermediate 52).

Aufarbeitung

  1. stirringUpon completion, stirring
  2. waitwas continued overnight at room temperature
  3. extractionThe product was extracted with 4-methyl-2-pentanone
  4. customThe extract was dried
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by column chromatography (HPLC) over silica gel using
  8. additiona mixture of dichloromethane and methanol (98.75:1.25 by volume) as eluent
  9. customThe second faction was collected
  10. customthe eluent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-8ac978557b4942dd8db7d2fbfc8ff579
Quelldatensatz
uspto-grants-1987_08
Patentnummer
US04689330

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