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

HRID 579789

반응식

HRID 579789 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0a615afa610c4cda9bbe82e6143ee075
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04749702

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