2,2-Diethoxyethylamine → 2,2-Dimethoxy-n-[(1-methyl-1h-benzimidazol-2-yl)methyl]ethanamine

HRID 1174216

反応式

HRID 1174216 の反応式
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH:11]=O.[CH2:13]([O:15][CH:16]([O:19][CH2:20]C)[CH2:17][NH2:18])C.[BH3-]C#N.[Na+]>CO.C(O)(=O)C>[CH3:13][O:15][CH:16]([O:19][CH3:20])[CH2:17][NH:18][CH2:11][C:3]1[N:2]([CH3:1])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=1

参加物

6

反応物 3

HCID 695242,2-DiethoxyethylamineHCID 7620841-methyl-1H-1,3-benzodiazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 552185252,2-Dimethoxy-n-[(1-methyl-1h-benzimidazol-2-yl)methyl]ethanamine収率 77.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

A solution of 1-methyl-2-formylbenzimidazole (1 g) in methanol (27 mL) and acetic acid (0.54 mL) was treated with aminoacetaldehyde diethylacetal (0.9 g, 1 eq.) and NaCNBH3 (0.85 g, 2 eq.) at 25° C., stirred for 1 hour. The mixture was partitioned between water and ethyl acetate. The organic phase layer was separated, washed sequentially with saturated NaHCO3 and brine, and concentrated. The residue was chromatographed on silica gel, eluting with 8% methanol/dichloromethane to give the title compound (1.2 g 64% yield).

後処理

  1. customThe mixture was partitioned between water and ethyl acetate
  2. customThe organic phase layer was separated
  3. washwashed sequentially with saturated NaHCO3 and brine
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with 8% methanol/dichloromethane

出典と根拠

ORDレコード
ord-e5daae675dfb421997044dbe4d66607e
出典データセット
uspto-grants-2010_11
特許番号
US07834043B2

関連ノート

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