Dimethylformamide → HCID 13728694, compound

HRID 1731304Notes

Reaction equation

HRID 1731304 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[N:3]=1.C([Li])CCC.CN(C)[CH:28]=[O:29]>O1CCCC1>[Cl:20][C:17]1[CH:18]=[CH:19][C:14]([CH:8]([C:4]2[N:3]=[C:2]([CH:28]=[O:29])[CH:7]=[CH:6][CH:5]=2)[CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 13728693HCID 13728693, compoundHCID 178418339Butyllithium

Product 1

HCID 13728694HCID 13728694, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (-70°) solution of 2-bromo-6-(1-(4-chlorophenyl)-3-dimethylaminopropyl)pyridine (1.44 g) under nitrogen in dry tetrahydrofuran (50 mL) was added with stirring a solution of n-butyllithium (2.4 mL, 1.7M in hexane). After an additional 5 min at -70°, dry dimethylformamide (1.5 mL) was added dropwise during 2 min. The solution was allowed to warm and then quenched with water (5 mL). The solvents were removed under reduced pressure and the residue was dissolved in methylene chloride (50 mL). This solution was extracted with water (3×25 mL), dried (Na2SO4), and concentrated to give crude 6-(1-(4-chlorophenyl)-3-dimethylaminopropyl)2-pyridine carboxaldehyde (formyl proton δ 10.05, 60 MHz, CDCl3) which was chromatographed on reverse phase (C18, Waters Prep 500, 60:40/acetonitrile:water, K1 =6.3 (C18 ; 70:30/acetonitrile:water).

Workup

  1. temperatureto warm
  2. customquenched with water (5 mL)
  3. customThe solvents were removed under reduced pressure
  4. dissolutionthe residue was dissolved in methylene chloride (50 mL)
  5. extractionThis solution was extracted with water (3×25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-529e5457cccc4935b228000921644311
Source dataset
uspto-grants-1986_11
Patent number
US04621094

Reaction notes

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