Sodium Iodide → 1-(Anilinocarbonylmethyl)-4-methoxymethoxypiperidine

HRID 2257893ノート

反応式

HRID 2257893 の反応式
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].[CH3:12][O:13][CH2:14][O:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.[I-].[Na+].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[NH:5]([C:3]([CH2:2][N:19]1[CH2:20][CH2:21][CH:16]([O:15][CH2:14][O:13][CH3:12])[CH2:17][CH2:18]1)=[O:4])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 11485ChloroacetanilideHCID 15172750HCID 15172750、化合物

生成物 1

HCID 229236881-(Anilinocarbonylmethyl)-4-methoxymethoxypiperidine収率 90.5%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

1.7 ml of chloroacetyl chloride was dropwise added to a solution of 3.0 g of aniline hydrochloride and 7 ml of triethylamine in 30 ml of dichloromethane. The mixture was stirred at room temperature for 3 hours, then washed with water and a saturated aqueous sodium hydrogencarbonate solution in this order, and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was crystallized from ethyl acetate-n-hexane to obtain 2.45 g of N-(2-chloroacetyl)aniline as a light brown solid. A suspension of 2.45 g of the N-(2-chloroacetyl)-aniline, 2.8 g of 4-methoxymethoxypiperidine, 2.45 g of sodium iodide and 2.3 ml of triethylamine dissolved in 30 ml of acetonitrile was refluxed for 1.5 hours. The reaction mixture was diluted with ethyl acetate. The dilution was washed with water and dried with magnesium sulfate. The solvent was removed by distillation. The resulting residue was purified by a silica gel column chromatography (eluant: ethyl acetate: n-hexane=1:1) to obtain 3.64 g of 1-(anilinocarbonylmethyl)-4-methoxymethoxypiperidine as a lightyellow oil.

後処理

  1. temperaturewas refluxed for 1.5 hours
  2. washThe dilution was washed with water
  3. dry with materialdried with magnesium sulfate
  4. customThe solvent was removed by distillation
  5. customThe resulting residue was purified by a silica gel column chromatography (eluant: ethyl acetate: n-hexane=1:1)

出典と根拠

ORDレコード
ord-c7a9152c7ca0461cbef4d30f4d7dea39
出典データセット
uspto-grants-1997_08
特許番号
US05658926

反応ノート

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