Phenyl isocyanate → HCID 66750951, compound

HRID 534917Notes

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].[C:19]1([N:25]=[C:26]=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>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:26]([NH:25][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:27])[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 (0.120 g, 0.41 mmol) in pyridine (4.0 mL) was added phenyl isocyanate (0.055 g, 0.46 mmol) and the reaction mixture was heated to 50° C. After 18 h the reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography (silica gel, 90:10 to 0:100 heptane/ethyl acetate, gradient elution) to provide 4-(2-tert-butylphenyl)-N-phenylpiperazine-1-carboxamide (0.093 g, 67%) as an off-white solid, mp 68-72° C.

Workup

concentrationAfter 18 h the reaction mixture was concentrated under reduced pressure
customthe residue was purified by flash column chromatography (silica gel, 90:10 to 0:100 heptane/ethyl acetate, gradient elution)

Sources & evidence

ORD record: ord-b607fdd6bf0341c2b72b7bbd3a7bc67c
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853215B2

Reaction notes

Loading…