N-Methylbenzylamine → 4-(N-benzyl-N-methylaminoacetyl)pyridine

HRID 275763

Reaction equation

HRID 275763 reaction equation
[CH2:1]([NH:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[O:14]>ClCCl>[CH2:1]([N:8]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)=[O:14])[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7669N-MethylbenzylamineHCID 27762394-(Bromoacetyl)pyridine hydrobromide

Product 1

HCID 700736314-(N-benzyl-N-methylaminoacetyl)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-benzyl-N-methylamine (3.7 cm3) in dry dichloromethane (40 cm3), cooled to 0° C. was added with stirring, 4-bromoacetylpyridine hydrobromide (4.0 g). The reaction was allowed to warm to room temperature, then stirred for a further 18 hr. The solvent was stripped at reduced pressure, and the residue partitioned between ethyl acetate and dilute aqueous Na2CO3. The organic phase was separated, dried (Na2SO4), evaporated, and the residue subjected to chromatography on silica gel, eluent 5% methanol in dichloromethane, to afford 4-(N-benzyl-N-methylaminoacetyl)pyridine, 1.49 g, 43%, as a yellow gum.

Workup

  1. additionwas added
  2. stirringstirred for a further 18 hr
  3. customthe residue partitioned between ethyl acetate and dilute aqueous Na2CO3
  4. customThe organic phase was separated
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-699ebe2269e54c3fa8fd56c24fea2b67
Source dataset
uspto-grants-2002_03
Patent number
US06352994B2

Linked notes

Loading…