Dichloromethane → 2-[6-(Azidomethyl)-2-pyridyl]propan-2-ol

HRID 2096677Notes

Reaction equation

HRID 2096677 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+].ClCCl>CN(C)C=O>[N:13]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1)=[N+:14]=[N-:15]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 33557Sodium AzideHCID 667183882-(6-(Bromomethyl)pyridin-2-yl)propan-2-ol

Product 1

HCID 866553202-[6-(Azidomethyl)-2-pyridyl]propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromomethyl-6-(1-hydroxy-1-methylethyl)pyridine (7.61 g, 33 mmol) was dissolved in dimethylformamide (100 mL) and sodium azide (2.6 g, 39.7 mmol) added. After stirring the resultant mixture overnight at ambient temperature, the reaction was poured into dichloromethane and washed well with water. The organic layer was dried (magnesium sulphate), filtered and concentrated to dryness. The resulting yellow oil (5.88 g, 93%) was used without further purification; NMR δH (400 MHz, CDCl3) 7.70 (1H, t, J 7.8 Hz), 7.30 (1H, d, J 8.0 Hz), 7.19 (1H, d, J 7.8 Hz), 4.82 (1H, br s), 4.42 (2H, s), 1.51 (6H, s); LC-MS Retention time 2.06 min, (M+H)+ 193.

Workup

  1. washwashed well with water
  2. dry with materialThe organic layer was dried (magnesium sulphate)
  3. filtrationfiltered
  4. concentrationconcentrated to dryness
  5. customThe resulting yellow oil (5.88 g, 93%) was used without further purification

Sources & evidence

ORD record
ord-c523b54b9acc4c47a3608f8b58e644d1
Source dataset
uspto-grants-2013_05
Patent number
US08450328B2

Reaction notes

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