P-Toluenesulfonamide → N-(1-benzyloxycarbonylpiperidin-4-ylmethyl)-4-methylphenylsulphonamide

HRID 1290545

反応式

HRID 1290545 の反応式
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.S(O[CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH2:22][CH2:21]1)(=O)(=O)C>O>[CH2:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][NH:13][S:10]([C:7]2[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=2)(=[O:12])=[O:11])[CH2:21][CH2:22]1)=[O:27])[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

参加物

5

反応物 3

HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 28820646Benzyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

生成物 1

HCID 18918451N-(1-benzyloxycarbonylpiperidin-4-ylmethyl)-4-methylphenylsulphonamide

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

Sodium hydride (300 mg of a 60% suspension) was added to a stirred solution of 4-methylphenylsulphonamide and the mixture stirred at room temperature until effervescence had ceased. N-benzyloxycarbonylpiperidine-4-methanol mesylate (1.09 g) was added and the mixture heated at 100° C. for 7 hours. After cooling to room temperature it was diluted with water (200 ml) and extracted with ether (4×40 ml); the extracts were combined, washed with water (2×) and brine, dried (MgSO4) and evaporated to yield N-(1-benzyloxycarbonylpiperidin-4-ylmethyl)-4-methylphenylsulphonamide; NMR (d6DMSO) δ 0.81-1.1(2H,m); 1.5-1.7(3H,m); 2.35(3H,s); 2.6(2H,t); 2.7-2.9(2H,m); 4.0(2H,d); 5.0(2H,s); 7.2-7.5(7H,m); 7.55(1H,t); 7.7(2H,d); m/e 403 (M+H)+.

後処理

  1. temperaturethe mixture heated at 100° C. for 7 hours
  2. temperatureAfter cooling to room temperature it
  3. extractionextracted with ether (4×40 ml)
  4. washwashed with water (2×) and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-35320a321c44418fac509d7b64b6c2c9
出典データセット
uspto-grants-1998_05
特許番号
US05750754

関連ノート

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