Morpholine → 4-[5-BRomo-3-(trifluoromethyl)pyridin-2-yl]morpholine

HRID 1820985Notes

Reaction equation

HRID 1820985 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=1.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>>[N:13]1([C:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([Br:12])=[CH:4][N:3]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 218363025-Bromo-2-chloro-3-(trifluoromethyl)pyridine

Product 1

HCID 688525644-[5-BRomo-3-(trifluoromethyl)pyridin-2-yl]morpholine

Conditions

Temperature
80 °C

Procedure

A mixture of 260 mg (1.0 mmol) of 2-chloro-3-trifluoromethyl-5-bromopyridine (from Step B) and 3 mL of morpholine was heated at 80° C. for 1 h. The mixture was cooled and concentrated. The residue was partitioned between 50 mL of CH2Cl2 and 1.0 N NaOH and the layers were separated. The organics were dried and concentrated. Chromatography on a Biotage 40S cartridge using 19:1 v/v hexanes/ether as the eluant afforded 290 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 3.29 (app t, J=5.5, 4H), 3.82 (app t, J=5.5, 4H); 7.95 (d, J=2.0, 1H), 8.45 (d, J=2.0, 1H.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. customThe residue was partitioned between 50 mL of CH2Cl2 and 1.0 N NaOH
  4. customthe layers were separated
  5. customThe organics were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7e376d40ad9d4c32a7c9b3072f5ab1f4
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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