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

HRID 1720295노트

반응식

HRID 1720295 반응식
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

참가 물질

7

반응물 4

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 11485ChloroacetanilideHCID 15172750HCID 15172750, 화합물

생성물 1

HCID 229236881-(Anilinocarbonylmethyl)-4-methoxymethoxypiperidine수율 90.5%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

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 light yellow oil.

후처리

  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)

출처 및 근거

ORD 기록
ord-7d564b8496cb4692a2fd5a5f4b890779
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05506239

반응 노트

불러오는 중…