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

HRID 2388028Notes

Reaction equation

HRID 2388028 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-cbb9d12fcdec44d48fe4f50bfa52b47a
Source dataset
uspto-grants-2012_09
Patent number
US08268992B2

Reaction notes

Loading…