Ammonium trifluoroacetate → 2-(4-Phenyl-1H-imidazol-2-yl)-4-(phenylmethyl)morpholine

HRID 2367351Notes

Reaction equation

O=[C:2]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][C:5]([CH:7]1[O:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:8]1)=O.FC(F)(F)C([O-])=O.[NH4+:33]>O>[C:20]1([C:2]2[N:33]=[C:5]([CH:7]3[O:12][CH2:11][CH2:10][N:9]([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH2:8]3)[NH:4][CH:3]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-(2-oxo-2-phenylethyl)-4-(phenylmethyl)-2-morpholinecarboxamide (850 mg, 2.51 mmol) and ammonium trifluoroacetate (1317 mg, 10.05 mmol) was heated at 150° C. under microwave condition with stirring for 1 hour. Water (150 mL) was added to the residue, and extracted with EtOAc (200 mL). The organic layer was dried (Na2SO4), filtered, and concentrated to afford the crude title compound (1.3 g) as a brown oil. This material was combined with another batch of crude title compound (250 mg) and purified by silica gel chromatography using as eluent EtOAc (1600 mL) in hexanes (400 mL) to afford the title compound (900 mg, 2.82 mmol) as a brown solid. LC-MS (ES) m/z=320 [M+H]+.

Workup

extractionextracted with EtOAc (200 mL)
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customto afford the crude title compound (1.3 g) as a brown oil
custompurified by silica gel chromatography

Sources & evidence

ORD record: ord-d72d6e100ac74509a3ec4e5c9b8fd2a1
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

Loading…