2-Morpholinoethylamine → HCID 24902952, compound

HRID 2218741Notes

Reaction equation

HRID 2218741 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 27363284-Bromo-1-fluoro-2-nitrobenzene

Product 1

HCID 24902952HCID 24902952, compoundYield 103%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Mix 5-bromo-2-fluoro-nitrobenzene (10 g, 45 mmol) and 4-(2-aminoethyl)morpholine (11.8 mL, 90 mmol) in THF (100 mL). Stir at room temperature for 18 h. Remove the THF under reduced pressure and partition the residue between water (200 mL) and ethyl acetate (200 mL). Dry the organic layer (MgSO4) and concentrate to give 15.3 g (100%) title compound. HPLC (ISO80-10M) t=1.83 min (94%), MS (S) 331 (M+1).

Workup

  1. customRemove the THF under reduced pressure
  2. custompartition the residue between water (200 mL) and ethyl acetate (200 mL)
  3. dry with materialDry the organic layer (MgSO4)
  4. concentrationconcentrate

Sources & evidence

ORD record
ord-5d840d6983b24be0bd903abd524e02c6
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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