2,5-Dimethylpyrrolidine → 4-(5-{[(cis)-2,5-Dimethyl-1-pyrrolidinyl]methyl}-1H-tetrazol-1-yl)benzonitrile

HRID 517771Notes

Reaction equation

HRID 517771 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH3:7])[NH:3]1.Cl[CH2:9][C:10]1[N:14]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[N:13]=[N:12][N:11]=1>C(#N)C>[CH3:1][C@H:2]1[CH2:6][CH2:5][C@@H:4]([CH3:7])[N:3]1[CH2:9][C:10]1[N:14]([C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[N:13]=[N:12][N:11]=1

Participants

4

Reactant 2

HCID 960342,5-DimethylpyrrolidineHCID 666554054-[5-(chloromethyl)-1H-tetrazol-1-yl]benzonitrile2×

Product 1

HCID 866918934-(5-{[(cis)-2,5-Dimethyl-1-pyrrolidinyl]methyl}-1H-tetrazol-1-yl)benzonitrileYield 48.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,5-dimethylpyrrolidine (0.334 mL, 2.73 mmol) and 4-[5-(chloromethyl)-1H-tetrazol-1-yl]benzonitrile (200 mg, 0.911 mmol, Intermediate 10) in acetonitrile (1.5 mL) was heated to 150° C. for 45 minutes in a microwave reactor. The reaction mixture was purified by high PH MDAP (2 injections). Relevant fractions were combined and the solvent removed. The resulting solid was partitioned between DCM (10 mL) and water (5 mL). The organic layer was collected via a hydrophobic frit and the solvent removed under vacuum to yield the title compound as a white solid (125 mg).

Workup

  1. customThe reaction mixture was purified by high PH MDAP (2 injections)
  2. customthe solvent removed
  3. customThe resulting solid was partitioned between DCM (10 mL) and water (5 mL)
  4. customThe organic layer was collected via a hydrophobic frit
  5. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-fd4dc97b9e594b749137ebca9e55aab0
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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