Hydrochloric Acid → 2,6-Difluoro-4-morpholin-4-yl-phenylamine

HRID 1158682

Reaction equation

HRID 1158682 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:6]=[C:7]([F:12])[C:8]=1[N+:9]([O-])=O>O1CCCC1.[Zn]>[F:12][C:7]1[CH:6]=[C:5]([N:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[CH:4]=[C:3]([F:2])[C:8]=1[NH2:9]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 668621544-(3,5-Difluoro-4-nitro-phenyl)-morpholine

Product 1

HCID 592443842,6-Difluoro-4-morpholin-4-yl-phenylamineYield 90%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Concentrated hydrochloric acid (4.2 mL) was added slowly to a mixture of zinc dust (3.3 g) and 4-(3,5-difluoro-4-nitro-phenyl)-morpholine (2.49 g) in tetrahydrofuran (40 mL) cooled to 0° C. The reaction mixture was then stirred for 1 hour at 0° C. and 2 hours at 25° C. The reaction mixture was filtered through Celite (10 g), concentrated in vacuo and purified by flash chromatography to furnish 1.96 g (90% yield) of the title compound as a white solid. GC-MS (fez) 214 (M); tR=5.83. 1H NMR (500 MHz, DMSO-d6): 2.94 (t, 4H), 3.69 (t, 4H), 4.53 (s, 2H), 6.57 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through Celite (10 g)
  2. concentrationconcentrated in vacuo
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-23050239762b4eac89f0644338fe1295
Source dataset
uspto-grants-2010_10
Patent number
US07812023B2

Linked notes

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