Morpholine → 4-(4-Chloro-2-methoxybenzyl)morpholine

HRID 272748Notes

Reaction equation

HRID 272748 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([Cl:9])=[CH:5][C:4]=1[O:10][CH3:11].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>C1(C)C=CC=CC=1>[Cl:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:4]([O:10][CH3:11])[CH:5]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 223274741-(Bromomethyl)-4-chloro-2-methoxybenzene

Product 1

HCID 692175364-(4-Chloro-2-methoxybenzyl)morpholineYield 93.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-bromomethyl-4-chloro-2-methoxy-benzene (705 mg), morpholine (0.52 mL, 6 mmol) in toluene (15 mL) was heated to 110° C. for 2 hours. The solution was then partitioned between ethyl acetate and water. The organic layer was washed with brine, dried (MgSO4), filtered, and concentrated under vacuum to provide 675 mg (93%) of the title compound. MS (ESI) m/e 242 (M+H)+.

Workup

  1. customThe solution was then partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-58123c9ce2ea42b7a57eccc0d614b280
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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