Allyl bromide → (+/-)-trans-1-Allyl-4-(4-bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine

HRID 1460082Notes

Reaction equation

HRID 1460082 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.[CH2:31](Br)[CH:32]=[CH2:33].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[CH2:33]([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:32]=[CH2:31]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 69942830(+/-)-trans-1-(4-Bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine

Product 1

HCID 69942692(+/-)-trans-1-Allyl-4-(4-bromo-alpha-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazineYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The purified benzhydrylpiperazine (41.0 g, 83.7 mmol) was dissolved in 500 mL of dry tetrahydrofuran with 7.3 mL (84 mmol) of allyl bromide and 22 g (200 mmol) of sodium carbonate and heated at reflux overnight under nitrogen. The cooled reaction solution was filtered and the solvent removed to give 44.1 g of crude (±)-trans-1-allyl-4-(4-bromo-α-(3-(tert-butyldimethylsilyloxy)phenyl)benzyl)-2,5-dimethylpiperazine as a brown oil. NMR (200 MHz, CDCl3): δ 0.15 (s,6H) 0.95 (m,12H); 1.15 (2 overlapping d,J=6 Hz,3H); 1.8 (m,1H); 2.1 (m,1H); 2.35-2.65 (m,3H); 2.7-2.9 (m,2H); 3.35 (dd,J1 =5 Hz,J2 =12 Hz,1H); 5.0-5.2 (m,3H); 5.85 (m,1H); 6.6-7.5 (m,8H).

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-a6545f4e65064a27a595e6ed195b4358
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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