Triethylamine → HCID 43406070, compound

HRID 1459446Notes

Reaction equation

HRID 1459446 reaction equation
C([O:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](Cl)=[O:8])(=O)C.Cl.[NH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].C(N(CC)CC)C>C1C=CC=CC=1>[OH:4][C:5]1[C:13]([O:14][CH3:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7]([NH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11499324Methyl 6-aminohexanoate hydrochlorideHCID 53744163HCID 53744163, compound

Product 1

HCID 43406070HCID 43406070, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

2.3 g (10 mmol) of 2-acetoxy-3-methoxybenzoyl chloride dissolved in 18 ml of anhydrous benzene were dropwise added to the suspension of 1.80 g (10 mmol) methyl 6-aminohexanoate hydrochloride in 2.2 g (22 mmol) of anhydrous triethylamine and 18 ml of anhydrous benzene under nitrogen at room temperature while stirring. After boiling under reflux for 2 hours while stirring, the reaction mixture was cooled down, the precipitate was filtered by suction and the filtrate was evaporated. 20 ml of water were portionwise added to the residue, the solution was extracted with ethyl acetate, the organic phase was washed with 1 M hydrochloric acid and water, then dried. The solvent was evaporated under reduced pressure. The residue was purified by chromatography on a silica gel column by using a 3:4 mixture of petroleum ether and ethyl acetate to obtain 1.62 g (55%) of the title compound, m.p.: 69°-70° C.

Workup

  1. temperatureunder reflux for 2 hours
  2. stirringwhile stirring
  3. temperaturethe reaction mixture was cooled down
  4. filtrationthe precipitate was filtered by suction
  5. customthe filtrate was evaporated
  6. addition20 ml of water were portionwise added to the residue
  7. extractionthe solution was extracted with ethyl acetate
  8. washthe organic phase was washed with 1 M hydrochloric acid and water
  9. customdried
  10. customThe solvent was evaporated under reduced pressure
  11. customThe residue was purified by chromatography on a silica gel column
  12. additiona 3:4 mixture of petroleum ether and ethyl acetate

Sources & evidence

ORD record
ord-a21f84c65ba64153b51c9c193d44f041
Source dataset
uspto-grants-1998_12
Patent number
US05854250

Reaction notes

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