Ammonium Chloride → HCID 19707505, compound

HRID 726747

Reaction equation

HRID 726747 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][NH2:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C[Si]([N:22]=[C:23]=[O:24])(C)C.[Cl-].[NH4+]>O1CCCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][CH2:16][NH:17][C:23]([NH2:22])=[O:24])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 70696Trimethylsilyl isocyanateHCID 112763943-Cyclopentyloxy-4-methoxyphenethylamine

Product 1

HCID 19707505HCID 19707505, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-cyclopentyloxy-4-methoxyphenyl)ethylamine (0.47 g, 2.0 mmol) in tetrahydrofuran (10 mL) under an argon atmosphere was added trimethylsilyl isocyanate (0.42 mL, 3.1 mmol). The resulting mixture was heated at reflux for 1 h, was allowed to cool to room temperature and then was stirred overnight. The reaction mixture was again heated to reflux for an additional 5 h and allowed to cool to room temperature. Ammonium chloride was added, and the mixture was concentrated under reduced pressure. The residue was partitioned between methylene chloride and water. The organic extract was washed successively with 10%. hydrochloric acid and water and dried (potassium carbonate). Removal of the solvent in vacuo and purification of the residue by flash chromatography, eluting with 3% methanol/methylene chloride, provided the urea as a white solid: m.p. 136°-37° C. Analysis Calc. for C15H22 N2O3 : C 64.73, H 7.97, N 10.06; found: C 64.66, H 7.97, N 10.28.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1 h
  3. temperatureThe reaction mixture was again heated
  4. temperatureto reflux for an additional 5 h
  5. temperatureto cool to room temperature
  6. concentrationthe mixture was concentrated under reduced pressure
  7. customThe residue was partitioned between methylene chloride and water
  8. extractionThe organic extract
  9. washwas washed successively with 10%
  10. dry with materialhydrochloric acid and water and dried (potassium carbonate)
  11. customRemoval of the solvent
  12. customin vacuo and purification of the residue by flash chromatography
  13. washeluting with 3% methanol/methylene chloride

Sources & evidence

ORD record
ord-6d5a407952ad44ecbb7247c7bee4cd74
Source dataset
uspto-grants-1998_01
Patent number
US05710180

Linked notes

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