Benzyl Bromide → HCID 67329265, compound

HRID 538753Notes

Reaction equation

HRID 538753 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:21]=[CH:20][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:10]2)=[CH:6][CH:5]=1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:22]([C:11]1([C:16]([O:18][CH3:19])=[O:17])[C:12](=[O:15])[CH2:13][CH2:14][N:9]([CH2:8][C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:21][CH:20]=2)[CH2:10]1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 56687133HCID 56687133, compound

Product 1

HCID 67329265HCID 67329265, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

In a three-necked flask, under a azote atmosphere, sodium hydride (0.115 g, 60% in mineral oil, 2.871 mmol) was added at 0° C. by small portions to a solution of methyl 1-(4-chlorobenzyl)-4-oxopiperidine-3-carboxylate obtained above (0.809 g, 2.871 mmol) in 1.80 mL of anhydrous DMF. The resulting mixture was stirred 30 min at room temperature and then a solution of benzyl bromide (0.341 mL, 2.871 mmol) in 2.20 mL of anhydrous DMF was added. The reaction was followed by HPLC and UPLC-MS. After 24 h at room temperature, it was diluted with ethyl acetate. The organic phase was washed with H2O, brine, dried over Na2SO4 and concentrated in vacuo to give a yellow oil that was purified by flash chromatography (SiO2, petroleum ether:ethyl acetate 95:5 as eluent). Evaporation and drying in vacuo of the pure fractions gave pure methyl 3-benzyl-1-(4-chlorobenzyl)-4-oxopiperidine-3-carboxylate as a colorless oil. (0.623 g, 1.675 mmol, 58% yield). 372.2.

Workup

  1. waitAfter 24 h at room temperature
  2. washThe organic phase was washed with H2O, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto give a yellow oil that
  6. customwas purified by flash chromatography (SiO2, petroleum ether:ethyl acetate 95:5 as eluent)
  7. customEvaporation
  8. customdrying in vacuo of the pure fractions

Sources & evidence

ORD record
ord-35f3861e11514d4a9d9eeb277d27e84c
Source dataset
uspto-grants-2014_10
Patent number
US08865758B2

Reaction notes

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