Potassium Carbonate → N-Benzyloxycarbonyl-3-(3-chloropropoxy)-4-methoxybenzylamine

HRID 583110Notes

Reaction equation

HRID 583110 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH:29]([Cl:32])[CH2:30][CH3:31]>CC(=O)CC>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:31][CH2:30][CH2:29][Cl:32])[CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 36872Propane, bromochloro-HCID 11219914benzyl N-[(3-hydroxy-4-methoxyphenyl)methyl]carbamate

Product 1

HCID 19689413N-Benzyloxycarbonyl-3-(3-chloropropoxy)-4-methoxybenzylamineYield 91.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture comprising 20 g of N-benzyloxycarbonyl-3-hydroxy-4-methoxybenzylamine, 14.43 g of potassium carbonate, 16.44 g of bromochloropropane and 200 ml of 2-butanone, was refluxed under heating with stirring for 16 hours. The mixture was cooled to room temperature. Then, inorganic substances were filtered off, and the filtrate was distilled under reduced pressure. The obtained residue was extracted with chloroform, and the organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The obtained residue was crystallized from diethyl ether/n-hexane to obtain 23.19 g of the above-identified compound as white crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. filtrationThen, inorganic substances were filtered off
  4. distillationthe filtrate was distilled under reduced pressure
  5. extractionThe obtained residue was extracted with chloroform
  6. washthe organic layer was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customThe obtained residue was crystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-9f1fae5517de4c859a6d8f3ada811192
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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