3-(4-Fluorobenzoyl)propyl chloride → HCID 57664586, compound

HRID 1467890Notes

Reaction equation

[CH:1]1([N:4]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:7])=[O:6])[CH2:3][CH2:2]1.Cl[CH2:21][CH2:22][CH2:23][C:24]([C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=1)=[O:25]>CN(C=O)C>[CH:1]1([N:4]([CH:14]2[CH2:19][CH2:18][N:17]([CH2:21][CH2:22][CH2:23][C:24]([C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)=[O:25])[CH2:16][CH2:15]2)[S:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)(=[O:6])=[O:7])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 70 °C

Procedure

N-Cyclopropyl-N-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}benzenesulfonamide (39) was prepared as follows. A mixture of N-cyclopropyl-N-(4-piperidinyl)benzenesulfonamide (100 mg, 0.36 mmol), 4-chloro-4′-fluorobutyrophenone (79 mg, 0.39 mmol) and TEA (54 mg, 0.54 mmol) in DMF was heated at 70° C. for 36 hours. The solvent was removed and the crude product was purified on a silica gel column, eluting first with CH2Cl2, then with EtOAc and 10% MeOH/EtOAc, to afford the title compound 39 as an orange oil. 1H NMR (CDCl3): δ 8.006-7.956 (m, 2H), 7.868-7.844 (d, 2H), 7.599-7.556 (m, 1H), 7.535-7.490 (m, 2H), 7.147-7.089 (t, 2H), 3.855-3.773 (m, 1H), 2.950-2.871 (m, 4H), 2.421-2.330 (t, 2H), 2.020-1.772 (m, 7H), 1.518-1.454 (d, 2H), 0.950-0.910 (m, 2H), 0.730-0.682 (m, 2H). LC: 98%. MS (e/z): 446 (M+H+).

Workup

customN-Cyclopropyl-N-{1-[4-(4-fluorophenyl)-4-oxobutyl]piperidin-4-yl}benzenesulfonamide (39) was prepared
customThe solvent was removed
customthe crude product was purified on a silica gel column
washeluting first with CH2Cl2

Sources & evidence

ORD record: ord-558c39cbc3ca4d92a6e6b8c3a715ffd1
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000174B2

Reaction notes

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