Carbon Dioxide → N-(2-Aminoethyl)-N-(4-chlorophenyl)amine

HRID 618624Notes

Reaction equation

[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.O1[CH2:13][C:12](=O)[N:11]=[C-]1.C(=O)=O>>[Cl:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:13][CH2:12][NH2:11])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 280Carbon Dioxide

HCID 78124-Chloroaniline

HCID 532495662H-1,3-oxazol-2-id-4-one

Product 1

HCID 12666393N-(2-Aminoethyl)-N-(4-chlorophenyl)amineYield 70.9%

Conditions

Temperature: 160 °C

Procedure

The hydrochloride salt of 4-chloroaniline (6.2 g, 38 mmol) and 2-oxazolidone (3.29 g, 38 mmol) was suspended in a minimal amount of di(ethyleneglycol)methyl ether and the resulting suspension heated at 160° C. After 4 h CO2 evolution ceased and the reaction mixture was cooled to ambient temperature. The resulting solid was crystallized from EtOH/ether to yield 4.6 g (58%) of 4-chloroanilinoethylamine as its HCl salt. MS (CI) (M+H)+ at m/z 171. The free amine was prepared by partitioning the HCl salt between CH2Cl2 and NaHCO3 (sat.), drying the organic layer (Na2SO4), filtering and concentrating.

Workup

temperaturethe reaction mixture was cooled to ambient temperature
customThe resulting solid was crystallized from EtOH/ether

Sources & evidence

ORD record: ord-55b6d3a3faa14449aa851e2ccfb90c14
Source dataset: uspto-grants-1999_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05955440

Reaction notes

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