Benzyl Bromide → HCID 58109649, compound

HRID 2037587Notes

Reaction equation

HRID 2037587 reaction equation
[CH2:1]([C@@:4]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:1]([C@@:4]1([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[O:9][C:8](=[O:10])[N:7]([C@H:11]2[CH2:16][CH2:15][CH2:14][N:13]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:12]2)[CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 58109296HCID 58109296, compound

Product 1

HCID 58109649HCID 58109649, compoundYield 13.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (R)-6-allyl-6-(4-fluorophenyl)-3-((S)-piperidin-3-yl)-1,3-oxazinan-2-one (530 mg, 1.67 mmol) in DMF (10 mL) was added benzyl bromide (573 mg, 3.35 mmol) and K2CO3 (924 mg, 6.7 mmol), and the mixture was heated to 80° C. for 5 hours. The reaction was quenched by H2O. The layers were separated, and the aqueous phase was extracted with CH2Cl2. The combined organic layer was dried over Na2SO4 and concentrated. The residue was purified by preparative TLC to give (R)-6-allyl-3-((S)-1-benzylpiperidin-3-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (90 mg, 13%).

Workup

  1. customThe reaction was quenched by H2O
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with CH2Cl2
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-79d1c032fedf4911b709f7581e8c510c
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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