Toluene → 4-[3-(Benzyloxy)phenyl]morpholine

HRID 1360016Notes

Reaction equation

HRID 1360016 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11](Br)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.CC(C)([O-])C.[Na+].C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8083MorpholineHCID 27566381-(Benzyloxy)-3-bromobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 669700054-[3-(Benzyloxy)phenyl]morpholineYield 80%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

526 mg (2.0 mmol) of 1-(benzyloxy)-3-bromobenzene, 209 μl (2.4 mmol) of morpholine, 283 mg (2.8 mmol) of sodium t-butoxide, 9 mg (0.005 mmol) of tris(dibenzylidine acetone)dipalladium(0) and 19 mg (0.015 mmol) of (±)-BINAP were placed in a flask, 5 ml of toluene was added thereto, and the mixture was stirred at 80° C. for 20 hours. The reaction mixture was cooled to room temperature, 20 ml of ethyl acetate was added thereto, and filtered through Cellite. The resulting filtrate was concentrated under a reduced pressure, and the residue was subjected to column chromatography using 30% ethyl acetate/hexane as an eluent to obtain 430 mg (yield 80%) of 4-(3-(benzyloxy)phenyl)morpholine.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered through Cellite
  3. concentrationThe resulting filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-b59239b20ef34a229d928398e9dd06cd
Source dataset
uspto-grants-2011_02
Patent number
US07879835B2

Reaction notes

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