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

HRID 2060588Notes

Reaction equation

HRID 2060588 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 3

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

Product 1

HCID 234381474-((6-Bromopyridin-2-yl)methyl)morpholine

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolventHCID 10340Sodium CarbonateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of 6-bromopyridine-2-carbaldehyde (3 g, 16.13 mmol) and morpholine (1.405 ml, 16.13 mmol) in 1,2-dichloroethane (22 ml) under argon was charged with sodium triacetoxyborohydride (4.79 g, 22.58 mmol) and allowed to stir for 14 hours. The reaction mixture was then diluted with ethyl acetate (100 mL), saturated aqueous sodium bicarbonate (60 mL), and saturated aqueous sodium carbonate (90 mL). The layers were separated and the organic layer was washed with saturated aqueous sodium bicarbonate (2×50 mL) and brine (2×50 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting material was purified by silica gel chromatography (30-100% ethyl acetate/hexanes) which afforded the title compound. LRMS (APCI) calc'd for C10H13BrN2O [M+1]+: 257, Found: 257.

Workup

  1. customThe layers were separated
  2. washthe organic layer was washed with saturated aqueous sodium bicarbonate (2×50 mL) and brine (2×50 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting material was purified by silica gel chromatography (30-100% ethyl acetate/hexanes) which

Sources & evidence

ORD record
ord-f98b00de76474949a7b84dbdbead82cc
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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