Methanol → 1-(4-Bromopyridin-2-yl)-4-methoxybutylamine

HRID 656234Notes

Reaction equation

HRID 656234 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]#[N:9])[CH:3]=1.[CH3:10][O:11][CH2:12][CH2:13][CH2:14][Mg]Cl.CO.[BH4-].[Na+]>O1CCCC1.C(OCC)(=O)C.[OH-].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([NH2:9])[CH2:14][CH2:13][CH2:12][O:11][CH3:10])[CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6932834-Bromo-2-cyanopyridineHCID 4311764Sodium borohydrideHCID 178495109HCID 178495109, compound

Product 1

HCID 686532511-(4-Bromopyridin-2-yl)-4-methoxybutylamine

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4.3 g of 4-bromopyridine-2-carbonitrile [62150-45-2] in 10 ml of tetrahydrofuran is added to a solution of 8.79 g of 3-methoxypropylmagnesium chloride [14202-12-1] in 10 ml of tetrahydrofuran. The reaction solution is stirred at room temperature for 10 minutes and then 50 ml of methanol are added. 2.7 g of sodium borohydride are added to the solution over the course of 30 minutes, and the mixture is stirred at room temperature for 2.5 hours. It is diluted with ethyl acetate and basified with 1M sodium hydroxide solution. The phases are separated. The aqueous phase is extracted with ethyl acetate (2×). The combined organic phases are evaporated. The crude title compound is obtained as an orange oil from the residue. Rt=2.47 (Gradient I).

Workup

  1. stirringthe mixture is stirred at room temperature for 2.5 hours
  2. customThe phases are separated
  3. extractionThe aqueous phase is extracted with ethyl acetate (2×)
  4. customThe combined organic phases are evaporated

Sources & evidence

ORD record
ord-a1c57317014341488f111c2e9d8384fa
Source dataset
uspto-grants-2011_12
Patent number
US08071651B2

Reaction notes

Loading…