Iodoethane → HCID 20306030, compound

HRID 1732346Notes

Reaction equation

HRID 1732346 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[OH:19])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:20]([CH2:23]OC)OC.[H-].[Na+].C(I)C>CN(C)C=O.C(O)(C)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([O:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH2:20][CH3:23])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 20306007HCID 20306007, compound

Product 1

HCID 20306030HCID 20306030, compoundYield 536.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent3×

Procedure

N-Acetyl-4-(2-hydroxyphenethyloxy)piperidine (8.0 g.) and dimethoxyethane (0.3 g.) in dry dimethylformamide (50 ml.) were added dropwise to a stirred suspension of sodium hydride (2.96 g., 50% dispersion in mineral oil) in dry dimethylformamide (50 ml.). The suspension was stirred at room temperature for 3.5 hours, cooled to 0°-5° C. then a solution of ethyl iodide (9.6 g.) in dimethylformamide (25 ml.) added dropwise. The mixture was allowed to warm to room temperature (20° C.), then stirred at room temperature for 2 hours. Isopropanol (75 ml.) was added, the solvent removed in vacuo and the residue partitioned between chloroform and water. The chloroform layer was dried and the solvent evaporated in vacuo to give N-acetyl-4-(2-ethoxyphenethyloxy)piperidine (5.2 g.).

Workup

  1. temperaturecooled to 0°-5° C.
  2. temperatureto warm to room temperature (20° C.)
  3. stirringstirred at room temperature for 2 hours
  4. customthe solvent removed in vacuo
  5. customthe residue partitioned between chloroform and water
  6. dry with materialThe chloroform layer was dried
  7. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-9e1b1bf6a7e847c881847caef59785b0
Source dataset
uspto-grants-1980_12
Patent number
US04237138

Reaction notes

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