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

HRID 639798Notes

Reaction equation

HRID 639798 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH:13]=O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[CH2:15]([O:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[N:12]=[N:11][C:10]([CH2:13][N:23]3[CH2:22][CH2:21][N:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])[CH2:25][CH2:24]3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 84311-Piperazinecarboxylic acid, ethyl esterHCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 59424218HCID 59424218, compound

Product 1

HCID 11537602Ethyl 4-{[2-(3-chlorophenyl)-2H-tetrazol-5-yl]methyl}piperazine-1-carboxylateYield 46.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-(3-Chloro-phenyl)-2H-tetrazole-5-carbaldehyde (22.3 mg, 0.107 mmol) was dissolved in 1,2-dichloroethane under argon and ethyl-1-piperazine carboxylate (16.4 uL, 0.112 mmol) was added followed by sodium triacetoxy borohydride (31.8 mg, 0.150 mmol). The reaction was allowed to stir overnight. Ethyl acetate was added and the solution was washed with sodium bicarbonate (sat.), brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using 45% EtOAc/Hexanes and 100% EtOAc to yield the title compound as a white solid (17.4 mg, 46%). 1H NMR (CDCl3) δ (ppm): 8.190 (s, 1H); 8.070 (m, 1H); 7.469 (m, 2H); 4.139 (q, 2H); 3.983 (s, 2H); 3.541 (m, 4H); 2.604 (m, 4H); 1.263 (t, 3H).

Workup

  1. washthe solution was washed with sodium bicarbonate (sat.), brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-05bdfaf63fed4ee09655467473eb9d18
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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