Ethyl Acetate → 1-(tert-Butoxycarbonyl)-4-[2-(3-methylureido)phenoxymethyl]piperidine

HRID 914825Notes

Reaction equation

HRID 914825 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]=[C:25]=[O:26].O.N.C(OCC)(=O)C>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22][C:25]([NH:24][CH3:23])=[O:26])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 12228Methyl IsocyanateHCID 12896473Azane;hydrateHCID 22248383tert-Butyl 4-[(2-aminophenoxy)methyl]piperidine-1-carboxylate

Product 1

HCID 222481171-(tert-Butoxycarbonyl)-4-[2-(3-methylureido)phenoxymethyl]piperidineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 400 mg of 1-(tert-butoxycarbonyl)-4-(2-aminophenoxymethyl)piperidine in 10 ml of tetrahydrofuran, 458 mg of methyl isocyanate was added and the mixture was stirred overnight at room temperature. Ammonia water was added to the reaction solution and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then filtered with NH silica gel. The solvent was distilled off under reduced pressure to obtain the title compound (469 mg, 99% yield).

Workup

  1. additionwas added
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered with NH silica gel
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dfe883fe24e549e48ca6b07acc5294f9
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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