4-Fluorobenzoyl chloride → HCID 11337818, compound

HRID 970739Notes

Reaction equation

HRID 970739 reaction equation
[CH3:1][N:2]([CH3:16])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH2:4]1.[F:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([Cl:24])=[O:23])=[CH:20][CH:19]=1>>[ClH:24].[CH3:1][N:2]([CH3:16])[CH:3]1[CH2:8][CH2:7][C:6]([C:9]2[CH:10]=[C:11]([NH:15][C:22](=[O:23])[C:21]3[CH:25]=[CH:26][C:18]([F:17])=[CH:19][CH:20]=3)[CH:12]=[CH:13][CH:14]=2)=[CH:5][CH2:4]1

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 58852355HCID 58852355, compound

Product 1

HCID 11337818HCID 11337818, compound

Procedure

Use a method similar to example 1, use 3-(4-dimethylamino-cyclohex-1-enyl)-phenylamine (enantiomer 2, preparation 3, 169 mg, 0.78 mmol) and 4-fluorobenzoyl chloride (149 mg, 0.94 mmol) to provide 89 mg (34%) of the free base of the title compound: MS (ES): m/z=339.2 (M+H)+; 1H NMR (CDCl3): δ 7.91 (m, 3H), 7.69 (br, 1H), 7.50 (d, 1H), 7.33 (t, 1H), 7.18 (m, 3H), 6.13 (m, 1H), 2.51 (m, 4H), 2.37 (s, 6H), 2.13 (m, 2H), 1.57 (m, 1H). Hydrochloride salt: Anal. cal'd for C21H23FN2O.HCl.0.5H2O: C, 65.70; H, 6.56; N, 7.30. Found: C, 65.30; H, 6.16; N, 7.21.

Sources & evidence

ORD record
ord-1bf84912846547d9a1ddb625fe595917
Source dataset
uspto-grants-2007_12
Patent number
US07312236B2

Reaction notes

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