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

HRID 1459272Notes

Reaction equation

HRID 1459272 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

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-d0b0ad49c0f1485eb0cea5004f6243c1
Source dataset
uspto-grants-1998_12
Patent number
US05854234

Reaction notes

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