Morpholine → 4-((5-Bromopyridin-2-yl)methyl)morpholine

HRID 2353546Notes

Reaction equation

HRID 2353546 reaction equation
S(Cl)(Cl)=O.[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12]O)=[N:10][CH:11]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(Cl)Cl.C(Cl)(Cl)Cl>[Br:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:12][N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 8083MorpholineHCID 24386Thionyl ChlorideHCID 5200169(5-Bromopyridin-2-yl)methanol

Product 1

HCID 120852844-((5-Bromopyridin-2-yl)methyl)morpholineYield 85%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Thionyl chloride (0.57 g, 5 mmol) in DCM (2 mL) was added dropwise to a stirred solution of (5-bromo-pyridin-2-yl)-methanol (0.3 g, 1.59 mmol) in DCM (5 mL) while cooling to 0° C. The mixture was allowed to warm to room temperature and, after 1 h, evaporated to low volume in vacuo. The residue was dissolved in CHCl3, and a solution of morpholine (0.41 g, 5 mmol) in CHCl3 was added at 0° C. After 3 h, the reaction was completed. The solvent was evaporated and addition of ether afforded the target compound (85%) as a white solid. Calculated mass=257. Observed mass=258

Workup

  1. temperatureto warm to room temperature and, after 1 h
  2. customevaporated to low volume in vacuo
  3. dissolutionThe residue was dissolved in CHCl3
  4. customThe solvent was evaporated
  5. additionaddition of ether

Sources & evidence

ORD record
ord-ba811d440dd84d5daf677081a8b365ac
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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