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

HRID 1720295Notes

Reaction equation

HRID 1720295 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-7d564b8496cb4692a2fd5a5f4b890779
Source dataset
uspto-grants-1996_04
Patent number
US05506239

Reaction notes

Loading…