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

HRID 1788076Notes

Reaction equation

HRID 1788076 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.[CH:26]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1)([CH3:28])[CH3:27].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:39]4[CH2:40][CH2:41][N:36]([C:31]5[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=5[O:29][CH:26]([CH3:28])[CH3:27])[CH2:37][CH2:38]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 109440161-[2-(Propan-2-yloxy)phenyl]piperazineHCID 12992442Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl ester

Product 1

HCID 12992448[1-(4-Chloro-phenyl)-cyclobutyl]-{3-[4-(2-isopropoxy-phenyl)-piperazin-1-ylmethyl]-piperidin-1-yl}-methanoneYield 37%

Procedure

Compound 11 was prepared using the method described in Example 3, starting with compound 2 (1.0 g, 2.60 mmol), 1-(2-isopropoxyphenyl)piperazine (0.63 g, 2.86 mmol), and cesium carbonate (1.27 g, 3.90 mmol) to give 11 (0.49 g, 37%); C30H40ClN3O2, LRMS (m/z)=511 (MH+).

Workup

  1. customCompound 11 was prepared

Sources & evidence

ORD record
ord-e826ef96d0254473a066b1b2039e0662
Source dataset
uspto-grants-2009_03
Patent number
US07511141B2

Reaction notes

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