ethyl N-(4-ethoxyphenyl)carbamate → HCID 14514745, compound

HRID 1461726Notes

Reaction equation

HRID 1461726 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=O)[O:30]CC)=[CH:24][CH:23]=1)[CH3:20]>COC(C)C(O)C>[CH2:19]([O:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:9]=2)=[O:30])=[CH:24][CH:23]=1)[CH3:20]

Participants

4

Reactant 2

HCID 230720ethyl N-(4-ethoxyphenyl)carbamateHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine

Product 1

HCID 14514745HCID 14514745, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 5477903-Methoxy-2-butanolSolvent

Procedure

The mixture of 3-(3-piperidinomethylphenoxy)propylamine (4.7 g) and ethyl N-(4-ethoxyphenyl)carbamate (4.0 g) in 3-methoxy-2-butanol (20 ml) was refluxed for 6 hours and then concentrated under reduced pressure. The resulting residue was dissolved in dichloromethane, washed with water, diluted hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution successively and dried over magnesium sulfate. After removal of the solvent under reduced pressure, the resulting residue was purified by silica gel flash column chromatography to give the precipitate (0.9 g; yield 11.4%). This precipitate was recrystallized from ethanol to give the title compound (0.5 g), mp 109-111° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe resulting residue was dissolved in dichloromethane
  4. washwashed with water, diluted hydrochloric acid solution, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution successively
  5. dry with materialdried over magnesium sulfate
  6. customAfter removal of the solvent under reduced pressure
  7. customthe resulting residue was purified by silica gel flash column chromatography
  8. customto give the precipitate (0.9 g; yield 11.4%)
  9. customThis precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-dce161640d1e4d1aa1947f90eb5a1e8b
Source dataset
uspto-grants-1991_12
Patent number
US05077302

Reaction notes

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