2-Amino-5-chlorobenzophenone → 4-[1-[(6-Chloro-2-methyl-4-phenyl-3-quinolinyl)carbonyl]-4-piperidinyl]benzamide

HRID 1184026Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O.O=[C:18]([CH3:37])[CH2:19][C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]2[CH:36]=[CH:35][C:31]([C:32]([NH2:34])=[O:33])=[CH:30][CH:29]=2)[CH2:24][CH2:23]1)=[O:21].[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>C(O)C>[Cl:8][C:5]1[CH:4]=[C:3]2[C:2](=[CH:7][CH:6]=1)[N:1]=[C:18]([CH3:37])[C:19]([C:20]([N:22]1[CH2:27][CH2:26][CH:25]([C:28]3[CH:29]=[CH:30][C:31]([C:32]([NH2:34])=[O:33])=[CH:35][CH:36]=3)[CH2:24][CH2:23]1)=[O:21])=[C:9]2[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 82 °C

Procedure

To a solution of (2-amino-5-chlorophenyl)(phenyl)methanone (693 mg, 3.0 mmol) in ethanol (10 ml) was added 4-(1-(3-oxobutanoyl)piperidin-4-yl)benzamide (893 mg, 3.1 mmol) followed by ytterbium triflate (186 mg, 0.3 mmol). The mixture was heated at 82° C. for 12 hours. The reaction mixture was cooled to room temperature, and the white powder thus obtained was filtered off, washed with ethanol, ethyl acetate, and finally ether to provide 4-(1-(6-chloro-2-methyl-4-phenylquinoline-3-carbonyl)piperidin-4-yl)benzamide (1.1 g, 76%) as a free flowing white powder. 1H NMR (DMSO-d6, 400 MHz) δ: 1 Rotameric forms complicates spectrum, the major rotamer is described; δ 8.09 (d, 1H, J=8.9 Hz); 7.9 (bs, NH, 1H); 7.8 (m, 3H); 7.7-7.5 (m, 6H); 7.25 (bs, NH, 1H); 6.8 (app d, 2H); 4.5 (d, 1H, J=12.9 Hz); 3.4-3.3 (m, 1H); 3.38 (s, 3H); 3.13 (app t, 1H, J=12.9 Hz); 2.8-2.4 (m, 2H); 2.5 (s, 3H); 0.72 (m, 1H); 0.54 (m, 1H). LC MS (CI) shows M+H 484.

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe white powder thus obtained
filtrationwas filtered off
washwashed with ethanol, ethyl acetate, and finally ether

Sources & evidence

ORD record: ord-47a5c2eb7d544a3a9601eb6aad8f238c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08664399B2

Reaction notes

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