Methyl iodide → tert-Butyl 4-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

HRID 962741ノート

反応式

HRID 962741 の反応式
[H-].[Na+].I[CH3:4].[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[NH:20][C:19]2=[O:27])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CN(C=O)C>[C:5]([O:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([N:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[N:20]([CH3:4])[C:19]2=[O:27])[CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13046891tert-Butyl 4-(2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

生成物 1

HCID 21222103tert-Butyl 4-(3-methyl-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl)piperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 0.060 g of sodium hydride, 60% oil dispersion, 10 mL of DMF, 0.086 mL of iodomethane, and 0.4 g of 1,3-dihydro-1-(1-tert-butyloxycarbonylpiperidin-4-yl)-2H-benzimidazol-2-one was stirred for 12 h, then partitioned between 100 mL of chloroform and 50 mL of water. The chloroform extracts dried over MgSO4, and concentrated under reduced pressure. Trituration with hexane gave 0.38 g of 1,3-dihydro-1-(1-tert-butyloxycarbonylpiperidin-4-yl)-3-methyl-2H-benzimidazol-2-one as a crystalline solid: 1H NMR (300 MHz, CDCl3) 7.13-7.03 (m, 3H), 6.98 (d, 1H), 4.5 (m, 1H), 4.3 (br m, 2H), 3.4 (s, 3H), 2.85 (m, 4H), 2.3 (m, 2H), 1.8 (d, 2H), 1.5 (s, 91H).

後処理

  1. custompartitioned between 100 mL of chloroform and 50 mL of water
  2. dry with materialThe chloroform extracts dried over MgSO4
  3. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5aa7e6141d854d6394d1a1d912291f29
出典データセット
uspto-grants-1998_06
特許番号
US05760054

反応ノート

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