Ammonium trifluoroacetate → 2-[4-(3-Chlorophenyl)-1H-imidazol-2-yl]-4-(phenylmethyl)morpholine

HRID 2367358Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:8](=O)[CH2:9][NH:10][C:11]([CH:13]2[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14]2)=O)[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C([O-])=O.[NH4+:34]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:34]=[C:11]([CH:13]3[O:18][CH2:17][CH2:16][N:15]([CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH2:14]3)[NH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-[2-(3-chlorophenyl)-2-oxoethyl]-4-(phenylmethyl)-2-morpholinecarboxamide (350 mg, 0.939 mmol) and ammonium trifluoroacetate (615 mg, 4.69 mmol) was stirred for 2.5 hours at 150° C. Water (150 mL) was added to the residue, and the aqueous mixture was extracted with EtOAc (200 mL). The organic phase was dried (Na2SO4), filtered, and concentrated to afford the title compound (320 mg) as a brown oil. LC-MS (ES) m/z=354 [M+H]+.

Workup

extractionthe aqueous mixture was extracted with EtOAc (200 mL)
dry with materialThe organic phase was dried (Na2SO4)
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4d37e945ee9b4594a22f0b37a12f44c9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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