Potassium Carbonate → 3-[1-Ethyl-2-pyrrolidinyl]phenyl methylcarbamate

HRID 1654022Notes

Reaction equation

HRID 1654022 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH2:5][CH:4]1[C:8]1[CH:9]=[C:10]([OH:14])[CH:11]=[CH:12][CH:13]=1)[CH3:2].[CH3:15][N:16]=[C:17]=[O:18].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH3:15][NH:16][C:17](=[O:18])[O:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH:4]2[CH2:5][CH2:6][CH2:7][N:3]2[CH2:1][CH3:2])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12228Methyl IsocyanateHCID 233613123-[1-Ethyl-2-pyrrolidinyl]phenol

Product 1

HCID 152227983-[1-Ethyl-2-pyrrolidinyl]phenyl methylcarbamateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[1-ethyl-2-pyrrolidinyl]phenol (0.8 g) in dry tetrahydrofuran (40 ml) was added methyl isocyanate (0.26 ml) at ambient temperature, under nitrogen, with stirring for ten mins. Milled potassium carbonate was added and the reaction mixture was stirred for 4 hrs, and filtered through a pad of celite. The solids were washed with ethyl acetate, and the combined filtrates were concentrated. The residue was purified by flash column chromatography (silica gel, dichloromethane/0-30% methanol), and the eluant flushed through alumina (ethyl acetate) to give 1.0 g (96%) of product. Recrystallization from ether/petroleum ether gave the analytical sample, mp 67°-69° C.

Workup

  1. stirringthe reaction mixture was stirred for 4 hrs
  2. filtrationfiltered through a pad of celite
  3. washThe solids were washed with ethyl acetate
  4. concentrationthe combined filtrates were concentrated
  5. customThe residue was purified by flash column chromatography (silica gel, dichloromethane/0-30% methanol)
  6. customthe eluant flushed through alumina (ethyl acetate)

Sources & evidence

ORD record
ord-198f7662603d4108bad75407d6b65161
Source dataset
uspto-grants-1995_04
Patent number
US05405845

Reaction notes

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