N,N-Dimethylaniline → 6-Benzylpyridin-2-amine

HRID 849157

Reaction equation

HRID 849157 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]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 75812-(Phenylmethyl)pyridineHCID 24533Sodium amide

Product 1

HCID 939026-Benzylpyridin-2-amine

Procedure

Example 298 A) A sample of 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. The contents were allowed to cool and were partitioned between ether 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.

Workup

  1. temperatureto cool
  2. customwere partitioned between ether and water
  3. dry with materialThe ether layer was dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customleaving an oil
  6. customThe oil was purified by chromatography
  7. dissolutionThe purified material was dissolved in 1N HCl
  8. customtriturated with EtOAc

Sources & evidence

ORD record
ord-1d26b230ebcc4fa8ac3b368b912322b7
Source dataset
uspto-grants-2000_01
Patent number
US06011028

Linked notes

Loading…