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

HRID 579789ノート

反応式

HRID 579789 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of 8.7 part 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).

後処理

  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

出典と根拠

ORDレコード
ord-0a615afa610c4cda9bbe82e6143ee075
出典データセット
uspto-grants-1988_06
特許番号
US04749702

反応ノート

読み込み中…