Triethylamine → N-ethyl-N-[3-(methoxycarbonyl)propionyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine

HRID 1732989Notes

Reaction equation

HRID 1732989 reaction equation
[CH2:1]([NH:3][CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[CH2:5]1)[CH3:2].C(N(CC)CC)C.[CH3:23][O:24][C:25]([CH2:27][CH2:28][C:29](Cl)=[O:30])=[O:26]>C1C=CC=CC=1>[CH2:1]([N:3]([CH:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH3:15])[CH:10]=2)[CH2:5]1)[C:29](=[O:30])[CH2:28][CH2:27][C:25]([O:24][CH3:23])=[O:26])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 12843078N-ethyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine

Product 1

HCID 12843097N-ethyl-N-[3-(methoxycarbonyl)propionyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamineYield 91.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a mixture of 8.8 g of N-ethyl-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine, 6.1 g of triethylamine and 80 ml of anhydrous benzene, 7.1 g of 3-(methoxycarbonyl)-propionyl chloride dissolved in 10 ml of anhydrous benzene was added dropwise. After the resulting solution was heated for 2.5 hours at reflux, the solution was allowed to stand overnight at room temperature (about 25° C.). The reaction solution was washed with a 2N-HCl aqueous solution, water, a 2 N-NaOH aqueous solution and water in order, and dried over anhydrous sodium sulfate. Then, the solution was concentrated under reduced pressure to obtain 12.5 g of N-ethyl-N-[3-(methoxycarbonyl)propionyl]-6-methoxy-1,2,3,4-tetrahydro-2-naphthylamine as a pale-yellow oily product.

Workup

  1. additionwas added dropwise
  2. temperatureAfter the resulting solution was heated for 2.5 hours
  3. temperatureat reflux
  4. custom(about 25° C.)
  5. washThe reaction solution was washed with a 2N-HCl aqueous solution, water
  6. dry with materiala 2 N-NaOH aqueous solution and water in order, and dried over anhydrous sodium sulfate
  7. concentrationThen, the solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-38d16073cefe451086a1af31cdaf3753
Source dataset
uspto-grants-1980_12
Patent number
US04239903

Reaction notes

Loading…