Toluene → 5-Benzyloxy-5-(4-fluoro-phenyl)-1-morpholin-4-yl-pentan-1-one

HRID 1052893Notes

Reaction equation

HRID 1052893 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10](=[O:22])[CH2:11][CH2:12][CH2:13][CH:14]([OH:21])[N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:6][CH:5]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1(C)C=CC=CC=1>O1CCCC1.CCCCCC>[CH2:23]([O:22][CH:10]([C:7]1[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=1)[CH2:11][CH2:12][CH2:13][C:14]([N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)=[O:21])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 667135681-(4-Fluoro-phenyl)-5-hydroxy-5-morpholin-4-yl-pentan-1-one

Product 1

HCID 667126875-Benzyloxy-5-(4-fluoro-phenyl)-1-morpholin-4-yl-pentan-1-oneYield 84.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1.8 gms of Sodium hydride was taken in 50 ml of tetrahydrofuran at 0° C., to this 5 gms of 1-(4-Fluoro-phenyl)-5-hydroxy-5-morpholin-4-yl-pentan-1-one was added under nitrogen atmosphere and maintained for about 30 minutes. To the reaction mass 3.4 gms of benzyl bromide was added at 20-25° C. and stirred for about 6 hours. Quenched the reaction mass with hydrochloric acid and stirred for about 15 minutes. Separated the layers and extracted the reaction mass with ethyl acetate. Organic layer was separated and dried over sodium sulphate. Distilled off the solvent completely and isolated the compound by adding 7 ml of toluene and 35 ml of hexane. Filtered the compound, washed with hexane and dried at 35-40° C. to get 5.6 gms of 5-Benzyloxy-5-(4-fluoro-phenyl)-1-morpholin-4-yl-pentan-1-one.

Workup

  1. additionwas added under nitrogen atmosphere
  2. temperaturemaintained for about 30 minutes
  3. customQuenched the reaction mass with hydrochloric acid
  4. stirringstirred for about 15 minutes
  5. customSeparated the layers
  6. extractionextracted the reaction mass with ethyl acetate
  7. customOrganic layer was separated
  8. dry with materialdried over sodium sulphate
  9. distillationDistilled off the solvent completely
  10. customisolated the compound
  11. filtrationFiltered the compound
  12. washwashed with hexane
  13. customdried at 35-40° C.

Sources & evidence

ORD record
ord-59f095076d254d2bb580237d7b0d4a0d
Source dataset
uspto-grants-2016_07
Patent number
US09388440B2

Reaction notes

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