Water → HCID 63531668, compound

HRID 1894794Notes

Reaction equation

HRID 1894794 reaction equation
[CH3:1][NH:2][C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Na+].[Br:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH2:18]Br.O>O1CCCC1>[CH3:1][N:2]([CH2:18][C:17]1[CH:20]=[CH:21][CH:22]=[C:15]([Br:14])[CH:16]=1)[C:3](=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 699793-Bromobenzyl bromideHCID 12554948HCID 12554948, compound

Product 1

HCID 63531668HCID 63531668, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5 g (31.8 mmol) of N-methyloctanamide (1a) are added at 0° C. to a suspension of 1.4 g (35 mmol) of sodium hydride (60% in grease) in 60 mL of tetrahydrofuran. The reaction mixture is stirred for 30 minutes at room temperature and a solution of 8.9 g (35 mmol) of 3-bromobenzyl bromide in 15 mL of tetrahydrofuran is then added. The mixture is stirred for 16 hours at room temperature. The reaction is stopped by adding 100 mL of water and is then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on silica gel (75/25 heptane/ethyl acetate). 7.4 g of N-methyl-N-(3-bromobenzyl)octanamide are obtained. Yield=71%.

Workup

  1. stirringThe mixture is stirred for 16 hours at room temperature
  2. extractionis then extracted with ethyl acetate
  3. dry with materialdried over sodium sulfate
  4. customThe solvents are evaporated off
  5. customthe residue is then chromatographed on silica gel (75/25 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-17b9840b73dc45c7a92ac83dff9af375
Source dataset
uspto-grants-2013_08
Patent number
US08513297B2

Reaction notes

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