Morpholine → 4-((6-Bromopyridin-2-yl)methyl)morpholine

HRID 520476Notes

Reaction equation

HRID 520476 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[Br:15][C:16]1[N:21]=[C:20]([CH:22]=O)[CH:19]=[CH:18][CH:17]=1.[NH:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C([O-])(O)=O.[Na+]>ClCCCl>[Br:15][C:16]1[N:21]=[C:20]([CH2:22][N:24]2[CH2:29][CH2:28][O:27][CH2:26][CH2:25]2)[CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 516892Sodium BicarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 234381474-((6-Bromopyridin-2-yl)methyl)morpholineYield 68%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

NaBH(OAc)3 (68.5 g, 0.323 mol) was added to a solution of 6-bromopicolinaldehyde 62 (40 g, 0.22 mol) and morpholine 63 (20.9 g, 0.24 mol) in 1,2-dichloroethane (500 mL). The mixture was stirred at room temperature for 16 h. Saturated NaHCO3 (500 mL) was added and the mixture was extracted with EtOAc, washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography on silica gel eluting with petroleum ether:ethyl acetate (10:1) to give 64 (38 g, 68% yield).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel eluting with petroleum ether:ethyl acetate (10:1)

Sources & evidence

ORD record
ord-48cf5a70aafb4eb39c682dcea8db655f
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

Loading…