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

HRID 876549Notes

Reaction equation

HRID 876549 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 66 (40 g, 0.22 mol) and morpholine 67 (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 68 (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-4c043bffc6b8400dab62b6344b49f3a9
Source dataset
uspto-grants-2015_03
Patent number
US08987258B2

Reaction notes

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