Ethyl isocyanate → HCID 66792705, compound

HRID 534912Notes

Reaction equation

Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[CH2:19]([N:21]=[C:22]=[O:23])[CH3:20]>N1C=CC=CC=1>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:22]([NH:21][CH2:19][CH3:20])=[O:23])[CH2:15][CH2:14]1)([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 1-(2-tert-butylphenyl)piperazine dihydrochloride (0.12 g, 0.41 mmol) in pyridine (4.0 mL) was added ethyl isocyanate (0.036 g, 0.51 mmol) at room temperature and the reaction mixture was heated at 50° C. for 16 h. After this time, the reaction mixture was cooled to room temperature and concentration under reduced pressure. The residue was partitioned between ethyl acetate and 0.5 N hydrochloric acid (2×10 mL), separated and the organic layer was concentrated under reduced pressure. The residue was purified by flash column chromatography (silica gel, 1:9 to 1:1 ethyl acetate/heptanes) to provide 4-(2-tert-butylphenyl)-N-ethylpiperazine-1-carboxamide (0.092 g, 77%) as a white solid, mp 196-198° C.

Workup

temperatureAfter this time, the reaction mixture was cooled to room temperature
concentrationconcentration under reduced pressure
customThe residue was partitioned between ethyl acetate and 0.5 N hydrochloric acid (2×10 mL)
customseparated
concentrationthe organic layer was concentrated under reduced pressure
customThe residue was purified by flash column chromatography (silica gel, 1:9 to 1:1 ethyl acetate/heptanes)

Sources & evidence

ORD record: ord-4b8aad4943234155b9b9c51a0448a261
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

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