Triethylamine → HCID 19884947, compound

HRID 846198Notes

Reaction equation

HRID 846198 reaction equation
[C:1]1([CH:7]([NH2:22])[CH2:8][CH2:9][O:10][C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([CH3:21])=[CH:13][CH:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C1COCC1>[CH2:34]([O:33][C:31]([NH:22][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:8][CH2:9][O:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([CH3:21])=[CH:13][CH:12]=1)=[O:32])[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 19884969HCID 19884969, compound

Product 1

HCID 19884947HCID 19884947, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2.12 g (7.3 mmol) of 1-phenyl-3-(4-methyl-1-naphthalenyloxy)propanamine, 1.12 ml (8.0 mmol) of triethylamine and 100 ml of THF was cooled to approximately 0° C. under a nitrogen atmosphere. To the mixture was added 0.766 ml (8.0 mmol) of ethyl chloroformate dropwise. The resulting mixture was stirred at room temperature for approximately five and one-half hours and concentrated under vacuum. The residue was dissolved in diethyl ether, toluene and water. The mixture was extracted with diethyl ether. The organic extracts were combined, washed with water, 2N hydrochloric acid, water, 1N sodium hydroxide water, and a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The mixture was concentrated under vacuum to provide 2.74 g of the title compound.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in diethyl ether
  3. extractionThe mixture was extracted with diethyl ether
  4. washwashed with water, 2N hydrochloric acid, water, 1N sodium hydroxide water
  5. dry with materiala saturated sodium chloride solution and dried over anhydrous sodium sulfate
  6. concentrationThe mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-545b927710a74dc6853677f85227c6a8
Source dataset
uspto-grants-1992_08
Patent number
US05135947

Reaction notes

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