N,N-Dimethylaniline → 6-Benzylpyridin-2-amine
Reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2-].[Na+].C[N:17](C)C1C=CC=CC=1>>[NH2:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=1Participants
Procedure
2-benzylpyridine (Aldrich, 2.5 g, 0.015 mole), sodium amide (780 mg, 0.02 mole) and N, N-dimethylaniline (25 mL) were refluxed overnight. Contents were allowed to cool and partitioned between ether (Et2O) and water. The ether layer was dried (MgSO4) and concentrated in vacuo leaving an oil. The oil was purified by chromatography. The purified material was dissolved in 1N HCl, lyophilized, and triturated with EtOAc to give 2-amino-6-benzylpyridine as a white solid. This 2-amino-6-benzylpyridine (470 mg), 5% rhodium/carbon (250 mg), and glacial acetic acid (30 mL) were shaken at 55 psi hydrogen on a Parr hydrogenation apparatus overnight. More catalyst (300 mg) was added and contents were again shaken at 55 psi hydrogen overnight. Contents were filtered and the filtrate was concentrated in vacuo leaving a viscous oil (500 mg). The product was purified by C-18 reverse phase chromatography to give a white solid. The solid was dissolved in 1N HCl, lyophilized, and recrystallized from EtOH/EtOAc to give the desired as a white solid. The analysis of the product was found to be consistent with the proposed structure.
Workup
- temperatureto cool
- custompartitioned between ether (Et2O) and water
- dry with materialThe ether layer was dried (MgSO4)
- concentrationconcentrated in vacuo
- customleaving an oil
- customThe oil was purified by chromatography
- dissolutionThe purified material was dissolved in 1N HCl
- customtriturated with EtOAc
Sources & evidence
- ORD record
- ord-089492a7eef64d0baec5ad53d29ca8fe
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06043261
Reaction notes
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