Acetic Acid → 1-(4-chlorobenzyl)-5-((methyl(phenyl)amino)methyl)pyridin-2(1H)-one

HRID 1948203Notes

Reaction equation

HRID 1948203 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Cl:9][C:10]1[CH:25]=[CH:24][C:13]([CH2:14][N:15]2[C:20](=[O:21])[CH:19]=[CH:18][C:17]([CH:22]=O)=[CH:16]2)=[CH:12][CH:11]=1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:9][C:10]1[CH:25]=[CH:24][C:13]([CH2:14][N:15]2[CH:16]=[C:17]([CH2:22][N:2]([CH3:1])[C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH:18]=[CH:19][C:20]2=[O:21])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7515N-MethylanilineHCID 5049666Sodium triacetoxyborohydrideHCID 866149681-(4-Chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde

Product 1

HCID 589669621-(4-chlorobenzyl)-5-((methyl(phenyl)amino)methyl)pyridin-2(1H)-oneYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 7 Method A: A solution of N-methylbenzenamine (1 eq, 0.40 mmol, 0.04 mL) and 1-(4-chlorobenzyl)-6-oxo-1,6-dihydropyridine-3-carbaldehyde (1 eq, 0.40 mmol, 0.10 g) in CH2Cl2 (8 mL) was stirred for 10 min. at room temperature then AcOH (1 eq, 0.40 mmol, 0.02 mL) and NaBH(OAc)3 (1.5 eq, 0.60 mmol, 0.10 g) were added. The reaction mixture was stirred 3 hours at room temperature, was quenched with water and the aqueous phase was extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2) using CH2Cl2/MeOH 95/5 followed by crystallization in pentane/diisopropyl ether to afford 1-(4-chlorobenzyl)-5-((methyl(phenyl)amino)methyl)pyridin-2(1H)-one (0.12 mmol, 0.04 g, 29%) as a white solid.

Workup

  1. customwas quenched with water
  2. extractionthe aqueous phase was extracted with CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography (AIT Flashsmart prepacked column 25 g SiO2)
  7. customfollowed by crystallization in pentane/diisopropyl ether

Sources & evidence

ORD record
ord-14de7dbf8c81460398c839c022732c82
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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