Morpholine → HCID 67168765, compound

HRID 1506417Notes

Reaction equation

HRID 1506417 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:11](=O)[CH2:10][CH2:9][CH2:8][O:7][C:6]=2[CH:13]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:13]=1)[O:7][CH2:8][CH2:9][CH:10]=[C:11]2[N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 8083MorpholineHCID 103770258-Bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one

Product 1

HCID 67168765HCID 67168765, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 8-bromo-3,4-dihydrobenzo[b]oxepin-5(2H)-one (0.170 g, 0.705 mmol) and morpholine (0.307 mL, 3.53 mmol) in toluene (3 mL) at 0° C. was added titanium(IV) chloride (1.0 M in toluene) (0.388 mL, 0.388 mmol) dropwise. The ice-bath was removed, and the orange, heterogeneous reaction mixture was stirred at room temperature overnight. The reaction mixture was filtered under reduced pressure through a pad of CELITE®, which was then rinsed with toluene (3×10 mL). The pale yellow filtrate was concentrated under reduced pressure to give (E)-4-(8-bromo-2,3-dihydrobenzo[b]oxepin-5-yl)morpholine (0.182 g, 0.587 mmol, 83% yield) as a yellow oil.

Workup

  1. customThe ice-bath was removed
  2. filtrationThe reaction mixture was filtered under reduced pressure through a pad of CELITE®, which
  3. washwas then rinsed with toluene (3×10 mL)
  4. concentrationThe pale yellow filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1ab47c32a75148579e498df62c3e0bfa
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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