2,5-Dimethylpiperazine, trans- → trans-4-(alpha-(2,5-Dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)-n,n-dimethylbenzenesulfonamide

HRID 1460115Notes

Reaction equation

HRID 1460115 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:26]=[CH:27][CH:28]=1)[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[CH:16][CH:15]=1)Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:29][C@H:30]1[CH2:35][NH:34][C@H:33]([CH3:36])[CH2:32][NH:31]1>CN(C)C=O>[CH3:29][C@H:30]1[CH2:35][NH:34][C@H:33]([CH3:36])[CH2:32][N:31]1[CH:12]([C:14]1[CH:19]=[CH:18][C:17]([S:20]([N:23]([CH3:25])[CH3:24])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[C:11]1[CH:26]=[CH:27][CH:28]=[C:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:10]=1

Participants

4

Reactant 2

HCID 2206722,5-Dimethylpiperazine, trans-HCID 536555114-(3-(tert-butyldimethylsilyloxy)-alpha-chlorobenzyl)-N,N-dimethylbenzenesulfonamide

Product 1

HCID 131720132trans-4-(alpha-(2,5-Dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)-n,n-dimethylbenzenesulfonamideYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

The alcohol (88.8 g, 0.21 mol) was treated with thionyl chloride in dichloromethane as described in Example 1 to give 93.7 g of 4-(3-(tert-butyldimethylsilyloxy)-α-chlorobenzyl)-N,N-dimethylbenzenesulfonamide as a brown oil. The crude benzhydryl chloride (93.7 g, 0.21 mol) was combined with trans-2,5-dimethylpiperazine (71.8 g, 0.63 mol) in 400 mL of dimethylformamide and heated to 140° C. for 1 hour. The mixture was cooled to room temperature, poured into ice water and extracted with diethyl ether. The ether extracts were washed with 1M sodium hydroxide, water, and saturated aqueous sodium chloride, and dried over sodium sulfate. The solvent was removed and the residue was purified by chromatography on silica gel with dichloromethane:methanol to give 28.9 g (27%) of trans-4-(α-(2,5-dimethyl-1-piperazinyl)-3-(tert-butyldimethylsilyloxy)benzyl)-N,N-dimethylbenzenesulfonamide as a brown oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with diethyl ether
  3. washThe ether extracts were washed with 1M sodium hydroxide, water, and saturated aqueous sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customThe solvent was removed
  6. customthe residue was purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-f1bc6594b0f1481aaacf35f68fc1e4ec
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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