Tetrahydrofuran → (2s,5s)-1-Allyl-4-(4-bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine

HRID 1602914Notes

Reaction equation

HRID 1602914 reaction equation
[Br:1][C:2]1[CH:30]=[CH:29][C:5]([CH:6]([N:21]2[CH2:26][C@H:25]([CH3:27])[NH:24][CH2:23][C@@H:22]2[CH3:28])[C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:8]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O1C[CH2:40][CH2:39][CH2:38]1>>[CH2:40]([N:24]1[CH2:23][C@H:22]([CH3:28])[N:21]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][Si:14]([C:17]([CH3:19])([CH3:20])[CH3:18])([CH3:16])[CH3:15])[CH:8]=2)[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:30][CH:29]=2)[CH2:26][C@@H:25]1[CH3:27])[CH:39]=[CH2:38]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 57043709(2s,5s)-1-(4-Bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine

Product 1

HCID 57007006(2s,5s)-1-Allyl-4-(4-bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine

Procedure

The purified benzhydrylpiperazine (1.51 g, 3.1 mmol) was dissolved in 20 mL of dry tetrahydrofuran with 0.27 mL (3.2 mmol) of alkyl bromide and 1.6 g (15.5 mmol) of sodium carbonate and heated at reflux overnight under nitrogen. The cooled reaction solution was filtered and the solvent removed to give 1.62 g of crude (2S,5S)-1-allyl-4-(4-bromo-α-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine as a yellow oil.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight under nitrogen
  3. customThe cooled reaction solution
  4. filtrationwas filtered
  5. customthe solvent removed

Sources & evidence

ORD record
ord-c048ddc925054237b20aad2853af92db
Source dataset
uspto-grants-1999_11
Patent number
US05985880

Reaction notes

Loading…