Water → 4-(3-Bromophenyl)morpholine

HRID 396171

Reaction equation

HRID 396171 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Br[CH2:10][CH2:11][O:12][CH2:13][CH2:14]Br.C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:5]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 115623-BromoanilineHCID 21521Bis(2-bromoethyl) etherHCID 81531Diisopropylethylamine

Product 1

HCID 49612684-(3-Bromophenyl)morpholineYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

3-Bromoaniline (3.0 mL, 4.7 g, 28 mmol), 2-bromoethylether (4.2 mL, 7.7 g, 33 mmol) and diisopropylethylamine (15 mL, 11 g, 86 mmol) were dissolved in anhydrous DMF (20 mL) under inert gas atmosphere and heated to 100° C. for 6 h. After cooling to room temperature the mixture was poured into water (300 mL) and extracted with EtOAc. The combined organic layers were washed with brine, dried Na2SO4), filtered and evaporated to dryness. Purification of the residue by flash chromatography afforded 2.9 g (12 mmol, 43% yield) of 4-(3-bromophenyl)morpholine.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine, dried Na2SO4),
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-1c187fb966aa4e42b729832344ceba1e
Source dataset
uspto-grants-2003_08
Patent number
US06608052B2

Linked notes

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