Triethylamine → HCID 19860039, compound

HRID 2072659Notes

Reaction equation

Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:11]([C:16]1[CH:26]=[C:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:24]=[CH:23][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][NH2:22])[CH2:12][CH2:13][CH2:14][CH3:15].C(N(CC)CC)C>C(#N)C>[CH2:11]([C:16]1[CH:26]=[C:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH:24]=[CH:23][C:17]=1[O:18][CH2:19][CH2:20][CH2:21][NH:22][C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3])[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

Conditions

Temperature: 0 °C

Procedure

78.3 g (0.5 mol) of phenyl chloroformate was dissolved in 250 ml of acetonitrile. A mixed solution of 137 g (0.45 mol) of 3-(2,4-diamylphenoxy)propylamine, 69.5 ml of triethylamine and 250 ml of acetonitrile was added dropwise to the solution thus formed in about 3 hours with stirring while the latter was cooled with ice at a temperature of 0° C. After the dropwise addition was finished, the reaction temperature was raised to 25° C. 2 l of ice water was added to the admixture. The admixture was then extracted with chloroform. The chloroform was removed under reduced pressure. Methanol was added to the residual oily matter to obtain 150 g of 3-(2,4-diamylphenoxy)-1-phenoxycarbonylaminopropane.

Workup

customthus formed in about 3 hours
additionAfter the dropwise addition
temperaturethe reaction temperature was raised to 25° C
extractionThe admixture was then extracted with chloroform
customThe chloroform was removed under reduced pressure
additionMethanol was added to the residual oily matter

Sources & evidence

ORD record: ord-9cfb8d366a844aab9b08925727c85572
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04914003

Reaction notes

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