Morpholine → HCID 67168817, compound

HRID 1506356Notes

Reaction equation

HRID 1506356 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[CH2:7][CH2:6][CH2:5]2.[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1)=[CH:7][CH2:6][CH2:5]2

Participants

5

Reactant 2

HCID 8083MorpholineHCID 101050696-Bromo-1-tetralone

Product 1

HCID 67168817HCID 67168817, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

To 6-bromo-3,4-dihydronaphthalen-1(2H)-one (0.475 g, 2.110 mmol) in toluene (5 mL) was added morpholine (0.735 mL, 8.44 mmol) at room temperature. The reaction mixture was cooled to 0° C. and titanium tetrachloride (1.0 M in toluene) (1.161 mL, 1.161 mmol) was added over a period of 3 min. The brown heterogeneous reaction mixture was allowed to come to room temperature and stirred for 20 h. The reaction mixture was diluted with 5 mL of anhydrous toluene and filtered over a thin pad of CELITE®. The filter pad was washed with addition anhydrous toluene (2×10 mL). The pale yellow filtrate was concentrated under reduced pressure to yield 4-(6-bromo-3,4-dihydronaphthalen-1-yl)morpholine (0.580 g, 1.972 mmol, 93% yield) as an oil.

Workup

  1. customto come to room temperature
  2. filtrationfiltered over a thin pad of CELITE®
  3. washThe filter pad was washed with addition anhydrous toluene (2×10 mL)
  4. concentrationThe pale yellow filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-081a16e26c0a4c999bb2892137d392b8
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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