1,2-Dichloroethane → 4-[(5-Bromopyridin-3-yl)acetyl]morpholine

HRID 1892227Notes

Reaction equation

HRID 1892227 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.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(Cl)CCl.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.CC1(C)C(C2C=NC(C)=C([N+]([O-])=O)C=2)=CCNC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:11])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 189859944-[(5-Bromopyridin-3-yl)acetyl]morpholineYield 95%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 673367223',3',6-Trimethyl-5-nitro-1',2',3',6'-tetrahydro-3,4'-bipyridineSolvent

Procedure

To a solution of (5-bromopyridin-3-yl)acetic acid (1.00 g, 4.63 mmol) and morpholine (0.50 mL, 5.73 mmol) in DCM (50 mL) was added EDC (1.78 g, 9.30 mmol) and 1-hydroxybenzotriazole (1.25 g, 9.26 mmol). The reaction mixture was allowed to stir at rt for 50 min and then diluted with DCM (50 mL) and 1N HCl (100 mL). The organic solution was separated and discarded. The aqueous solution was neutralized with sat. aq. NaHCO3 (100 mL) and was extracted with DCM (3×50 mL). The organic solutions were combined, dried over MgSO4, filtered and concentrated to give 4-[(5-bromopyridin-3-yl)acetyl]morpholine (1.26 g, 4.40 mmol, 95%) as a light brown solid. LCMS (FA): Rt=1.11 min, m/z=287.0 (M+H).

Workup

  1. customThe organic solution was separated
  2. extractionwas extracted with DCM (3×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-359aa1526dc1435b83adfcedc197c6db
Source dataset
uspto-grants-2013_08
Patent number
US08507667B2

Reaction notes

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