Cesium carbonate → [1-(4-Chloro-phenyl)-cyclobutyl]-{3-[4-(2-trifluoromethoxy-phenyl)-piperazin-1-ylmethyl]-piperidin-1-yl}-methanone

HRID 50651Notes

Reaction equation

HRID 50651 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20]OS(C)(=O)=O)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[F:26][C:27]([F:42])([F:41])[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1.C(=O)([O-])[O-].[Cs+].[Cs+]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][N:38]4[CH2:39][CH2:40][N:35]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=5[O:28][C:27]([F:26])([F:41])[F:42])[CH2:36][CH2:37]4)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 10796Cesium carbonateHCID 107529251-(2-Trifluoromethoxyphenyl)piperazineHCID 12992442Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl ester

Product 1

HCID 12992447[1-(4-Chloro-phenyl)-cyclobutyl]-{3-[4-(2-trifluoromethoxy-phenyl)-piperazin-1-ylmethyl]-piperidin-1-yl}-methanoneYield 32.3%

Procedure

Compound 9 was prepared using the method described in Example 3, starting with compound 2 (1.0 g, 2.60 mmol), 1-(2-trifluoromethoxyphenyl)piperazine (0.70 g, 2.86 mmol), and cesium carbonate (1.27 g, 3.90 mmol) to give 9 (0.45 g, 32%); C28H33ClF3N3O 2, LRMS (m/z)=537 (MH+).

Workup

  1. customCompound 9 was prepared

Sources & evidence

ORD record
ord-ec20c25f373f4f919bcc3695d6c7e667
Source dataset
uspto-grants-2004_03
Patent number
US06713479B2

Reaction notes

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