Dimethylformamide → N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N-methyl-2-benzothiazolamine

HRID 1761507ノート

反応式

HRID 1761507 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][NH:19][C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:14][CH2:13]1.[CH3:29]N(C)C=O.[H-].[Na+].IC>O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][N:12]1[CH2:17][CH2:16][CH:15]([CH2:18][N:19]([CH3:29])[C:20]2[S:21][C:22]3[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=3[N:24]=2)[CH2:14][CH2:13]1

参加物

6

反応物 4

HCID 6228Dimethylformamide2 回HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 128556R 47243

生成物 1

HCID 14049018N-[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N-methyl-2-benzothiazolamine

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a stirred solution of 11.85 parts of N-[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinylmethyl]-2-benzothiazolamine in 72 parts of N,N-dimethylformamide were added portionwise 1.5 parts of a sodium hydride dispersion 50%. Upon completion, stirring was continued for 30 minutes. A solution of 4.6 parts of iodomethane in 18 parts of N,N-dimethylformamide was added dropwise. The whole was stirred overnight at room temperature. The reaction mixture was poured into water and the product was extracted twice with 4-methyl-2-pentanone. The combined organic layers were dried, filtered and evaporated. The residue was separated by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The first fraction was collected and the eluent was evaporated. The residue was crystallized from a mixture of acetonitrile and 1,1'-oxybisethane, yielding 1 part of N[[1-[(2,3-dihydro-1,4-benzodioxin-2-yl)methyl]-4-piperidinyl]methyl]-N-methyl-2-benzothiazolamine; mp. 125.4° C. (compound 62).

後処理

  1. stirringThe whole was stirred overnight at room temperature
  2. extractionthe product was extracted twice with 4-methyl-2-pentanone
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was separated by column chromatography over silica gel using
  7. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  8. customThe first fraction was collected
  9. customthe eluent was evaporated
  10. customThe residue was crystallized from a mixture of acetonitrile and 1,1'-oxybisethane

出典と根拠

ORDレコード
ord-cee98460aac74caa8ccfe1cc6fbbdc7b
出典データセット
uspto-grants-1989_05
特許番号
US04826848

反応ノート

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