Dichloromethane → 4-(6-Chloropyridine-3-carbonyl)morpholine

HRID 494794Notes

Reaction equation

HRID 494794 reaction equation
Cl[C:2]1[N:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C(N(CC)CC)C.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.[Cl:24]CCl>>[Cl:24][C:9]1[N:10]=[CH:2][C:3]([C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[O:5])=[CH:7][CH:8]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 8471TriethylamineHCID 27745412-Chloronicotinoyl chloride

Product 1

HCID 8574994-(6-Chloropyridine-3-carbonyl)morpholineYield 88%

Procedure

To a solution of chloronicotinoyl chloride (3.52 g, 2.00 mmol) and triethylamine (3.1 mL, 2.22 mmol) in dichloromethane (5 mL) at 0° C. was slowly added morpholine (1.75 mL, 2.00 mmol). The mixture was warmed to ambient temperature, washed with water (2×25 mL), brine (1×25 mL), dried (Na2SO4), filtered and concentrated under reduced pressure. The product was chromatographed on silica with ethyl acetate to give the titled compound (4.0 g, 88%). MS (DCI) m/z 227 (M+H)+;

Workup

  1. customat 0° C.
  2. washwashed with water (2×25 mL), brine (1×25 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe product was chromatographed on silica with ethyl acetate

Sources & evidence

ORD record
ord-68c9f0cd96684743ad5d1c5c361cfd4d
Source dataset
uspto-grants-2009_05
Patent number
US07538138B2

Reaction notes

Loading…