1-Piperazinecarboxylic acid, ethyl ester → Ethyl 4-{1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethyl}piperazine-1-carboxylate

HRID 639800Notes

Reaction equation

HRID 639800 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13](OS(C)(=O)=O)[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26]([O:28][C:29]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)=[O:30])[CH3:27]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]([N:34]3[CH2:33][CH2:32][N:31]([C:29]([O:28][CH2:26][CH3:27])=[O:30])[CH2:36][CH2:35]3)[CH3:14])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 11430Potassium CarbonateHCID 75292157methanesulfonic acid 1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]-ethyl ester

Product 1

HCID 68429673Ethyl 4-{1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]ethyl}piperazine-1-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound (12.3 mg, 37%, yellow oil) was prepared from methyl sulfonic acid 1-[2-(3-chlorophenyl)-2H-tetrazol-5-yl]-ethyl ester (27.7 mg, 0.091 mmol) using potassium carbonate (13.8 mg, 0.100 mmol) and 1-ethoxycarbonyl piperazine (13.3 uL, 0.091 mmol) in acetonitrile (4 mL) at 80° C. overnight. The product was purified was by chromatography using a silica SPE tube (10% MeOH/CH2Cl2) followed by a second chromatography using a silica SPE tube (5% MeOH/CH2Cl2). 1H NMR (CDCl3) δ (ppm): 8.17 (s, 1H), 8.07 (dt, 1H), 7.50 (m, 2H), 4.29 (q, 1H), 4.10 (q, 2H), 3.52 (m, 4H), 2.56 (m, 4H), 1.64 (d, 3H), 1.24 (t, 3H).

Workup

  1. customat 80° C.
  2. customovernight
  3. customThe product was purified

Sources & evidence

ORD record
ord-a680214452bd46a98783f725a85fbe36
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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