Sodium hydride → HCID 58456423, compound

HRID 1040180Notes

Reaction equation

HRID 1040180 reaction equation
[Br:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][NH:4][C:3]1=[O:9].[H-].[Na+].Br[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1>O1CCCC1>[Br:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:3]1=[O:9]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1650214-Methoxybenzyl bromideHCID 110306353-Bromoazepan-2-one

Product 1

HCID 58456423HCID 58456423, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromoazepan-2-one (1.398 g, 7.28 mmol) in tetrahydrofuran (10 ml), was added sodium hydride (0.48 g, 12.00 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour, and 1-(bromomethyl)-4-methoxybenzene (1.610 g, 8.01 mmol) was added. The mixture was warmed to room temperature over the span of 2 hours. The reaction was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried and concentrated to afford crude product, which was purified by chromatography on silica gel (ethyl acetate/hexanes=2/8) to afford 3-bromo-1-(4-methoxybenzyl)azepan-2-one (1.403 g, 4.49 mmol, 61.7% yield). MS ESI: [M+H]+ m/z 313.2.

Workup

  1. temperatureThe mixture was warmed to room temperature over the span of 2 hours
  2. customThe reaction was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customto afford crude product, which
  8. customwas purified by chromatography on silica gel (ethyl acetate/hexanes=2/8)

Sources & evidence

ORD record
ord-c06cff3fc48c487e89987fb7b40ad25b
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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