3-(4-Fluorobenzoyl)propyl chloride → HCID 10309785, compound

HRID 350802Notes

Reaction equation

[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[CH:12]4[CH2:18][CH2:17][NH:16][CH2:15][CH2:14][CH:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1.Cl[CH2:20][CH2:21][CH2:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=[O:24].CCN(C(C)C)C(C)C>O1CCOCC1>[CH3:1][N:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]3[CH:12]4[CH2:18][CH2:17][N:16]([CH2:20][CH2:21][CH2:22][C:23]([C:25]5[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=5)=[O:24])[CH2:15][CH2:14][CH:13]4[N:5]([C:6]=23)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 96 °C

Procedure

3-Methyl-2,3,7,8,9,10,11,11a-octahydro-1H,6bH-azepino[4′,5′:4,5]pyrrolo[1,2,3-de]quinoxaline (72 mg, 0.3 mmol), 4-chloro-4′-flourobutyrophenone (119 mg, 0.6 mmol), KI (49 mg, 0.3 mmol), and DIEA (383 mg, 3 mmol) were added to dioxane (2.5 mL). The suspension was stirred at 96° C. for 18 hrs. The reaction was cooled to rt and then concentrated. The residue was purified by column chromatography (5–10% MeOH/CH2Cl2), to afford the title compound (37.5 mg, 31%) as an oil. The enantiomers of the title compound were separated on a Chiracel OD column using 8% EtOH-Hexane as the eluent. 1H NMR (CDCl3, 300 MHz) δ 7.9–8.1 (2H, m), 7.1–7.2 (2H, m), 6.6–6.7 (1H, m), 6.3–6.5 (2H, m), 2.7–3.8 (19H, m), 1.9–2.3 (4H, m) ppm. MS (ESI): 408.3 (base, M+H)

Workup

temperatureThe reaction was cooled to rt
concentrationconcentrated
customThe residue was purified by column chromatography (5–10% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-ff573e0db56f447fa1de7a9a851c9091
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183282B2

Reaction notes

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