HCID 22219602, compound → HCID 22219618, compound

HRID 1793804Notes

Reaction equation

B1([O-])OO1.[OH2:5].[OH2:6].O.O.[Na+].[F:10][C:11]([F:27])([F:26])[C:12]([N:14]1[CH2:20][CH2:19][C:18]2[CH:21]=[CH:22][CH:23]=[C:24]([NH2:25])[C:17]=2[CH2:16][CH2:15]1)=[O:13]>C(O)(=O)C>[N+:25]([C:24]1[C:17]2[CH2:16][CH2:15][N:14]([C:12](=[O:13])[C:11]([F:10])([F:26])[F:27])[CH2:20][CH2:19][C:18]=2[CH:21]=[CH:22][CH:23]=1)([O-:6])=[O:5]

Participants

Conditions

Temperature: 55 °C

Procedure

Under N2, a flame-dried, 100-mL, three-necked flask is charged with sodium perborate tetrahydrate (5.75 g, 37.4 mmol) and acetic acid (20 mL) and heated to 50–60° C. using an oil bath. A solution of 3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-6-amine (1.93 g, 7.5 mmol) in acetic acid (20 mL) was slowly added drop-wise over 30 min. The mixture is heated at 55° C. for 1 hour. The mixture was filtered and partitioned between CH2Cl2 and water. The organic layer is washed with water and concentrated to give 2.24 g of an amber oil. Column chromatography (elution with 10–25% EtOAc/heptane) gives 1.52 g (70%) of the title compound as a yellow oil. An analytical sample was crystallized from EtOAc/hexane to give off-white crystals: mp 64–67° C.; 1H NMR (400 MHz, CDCl3) δ 7.63 (d, J=8 Hz, 1 H), 7.41–7.29 (m, 2 H), 3.89–3.74 (m, 4 H), 3.15–3.10 (m, 4 H); IR (diffuse reflectance) 1687, 1523, 1466, 1451, 1376, 1368, 1295, 1197, 1186, 1179, 1168, 1147, 950, 818, 752 cm−1; MS (EI) m/z 288 (M+); Anal. Calcd for C12H11F3N2O3: C, 50.01; H, 3.85; N, 9.72; F, 19.77. Found: C, 49.95; H, 3.88; N, 9.68.

Workup

temperatureheated to 50–60° C.
customover 30 min
filtrationThe mixture was filtered
custompartitioned between CH2Cl2 and water
washThe organic layer is washed with water
concentrationconcentrated

Sources & evidence

ORD record: ord-83f979a6e69d412384847d7db87f5b55
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07022694B2

Reaction notes

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