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

HRID 1531820

Reaction equation

HRID 1531820 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-2de880554d7644f69b61d9ba078c0f35
Source dataset
uspto-grants-2001_03
Patent number
US06200982B1

Linked notes

Loading…