2-Methylpyrrolidine → Racemic 4-{2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-benzooxazol-5-yl}benzonitrile

HRID 900198

Reaction equation

HRID 900198 reaction equation
[CH:1]([C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)=[CH:8][C:6]=2[N:7]=1)=[CH2:2].[CH3:20][CH:21]1[CH2:25][CH2:24][CH2:23][NH:22]1>C(O)C>[CH3:20][CH:21]1[CH2:25][CH2:24][CH2:23][N:22]1[CH2:2][CH2:1][C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 130032-MethylpyrrolidineHCID 219800914-(2-Vinyl-benzooxazol-5-yl)-benzonitrile

Product 1

HCID 11174938Racemic 4-{2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-benzooxazol-5-yl}benzonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 24.6 mg (0.1 mmol) of 4-(2-vinyl-benzooxazol-5-yl)-benzonitrile and 24 mg of racemic 2-methyl-pyrrolidine (Aldrich, CAS #765-38-8) in 0.25 mL of ethanol was stirred at room temperature for 1 hour, then concentrated in vacuo to a glass to give pure product racemic 4-{2-[2-(2-methyl-pyrrolidin-1-yl)-ethyl]-benzooxazol-5-yl}-benzonitrile 33 mg (100%): 1H NMR (300 MHz, CDCl3) δ 7.85 (d, J=1.8 Hz, 1 H), 7.77 (d, J=8.4 Hz, 2 H), 7.70 (d, J=8.4 Hz, 2 H), 7.58 (d, J=7.5 Hz, 1 H), 7.50 (dd, J=7.5, 1.8 Hz), 3.2-3.32 (m, 4 H), 1.44-2.65 (m, 7 H), 1.15 (m, 3 H); Mass spectrum: [M+H]+ 332.1.

Workup

  1. concentrationconcentrated in vacuo to a glass

Sources & evidence

ORD record
ord-d466bab078774637ada00123d5fcdd98
Source dataset
uspto-grants-2008_04
Patent number
US07358263B2

Linked notes

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