Water → 4-But-3-enyl-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one

HRID 1096234Notes

Reaction equation

HRID 1096234 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([N:9]2[CH2:15][CH2:14][C:13](=[O:16])[NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1.Br[CH2:20][CH2:21][CH:22]=[CH2:23].[H-].[Na+].O>CN(C=O)C>[CH2:23]([N:12]1[C:13](=[O:16])[CH2:14][CH2:15][N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:17])[F:18])[CH:4]=2)[CH2:10][CH2:11]1)[CH2:22][CH:21]=[CH2:20]

Participants

6

Reactant 4

HCID 962WaterHCID 21241Homoallyl bromideHCID 24758Sodium hydrideHCID 217545091-(3-Trifluoromethyl-phenyl)-[1,4]diazepan-5-one

Product 1

HCID 667830254-But-3-enyl-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-oneYield 28.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one 0.29 g (1 mmol) and 4-bromobut-1-ene 0.3 g (2 mmol) in DMF (2 ml) was added NaH 0.1 g (2 mmol of 55% dispersion in oil) and the mixture stirred for 6 h. The reaction was then poured into water and extracted with EtOAc, dried (Na2SO4) and concentrated. Purification by flash column chromatography (EtOAc/n-heptane 1:1) afforded the title compound 0.09 g (25%) as a yellow gum. MS: 313.2 (MH+).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customPurification by flash column chromatography (EtOAc/n-heptane 1:1)

Sources & evidence

ORD record
ord-98c2e04498b14106a3ad2e17fdabe32d
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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