Morpholine → 4-[(5-Bromopyridin-3-yl)acetyl]morpholine

HRID 712762Notes

Reaction equation

HRID 712762 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[CH:5]=[N:6][CH:7]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 189859944-[(5-Bromopyridin-3-yl)acetyl]morpholine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 5-bromo-3-pyridineacetic acid (500 mg, 2.314 mmol) in DMF (3 mL) is added TBTU (1.11 g, 3.472 mmol). Morpholine (0.61 mL, 6.94 mmol) is added dropwise and the mixture is stirred at room temperature for 18 h. The mixture is diluted with EtOAc (50 mL), washed with water (3×5 mL), and brine, dried over sodium sulfate, filtered, and concentrated. The resulting crude product is purified by normal phase chromatography using 0-4.5% MeOH in DCM as the gradient to afford 2-(5-bromo-pyridin-3-yl)-1-morpholin-4-yl-ethanone.

Workup

  1. washwashed with water (3×5 mL), and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting crude product is purified by normal phase chromatography

Sources & evidence

ORD record
ord-9716dbba41f443b7ba5e7771cc66c647
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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