4-Toluenesulfonyl chloride → HCID 86709367, compound

HRID 2172232Notes

Reaction equation

HRID 2172232 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:27])([CH3:26])[CH2:23][CH2:24][OH:25])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:28](Cl)([C:31]1[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=1)(=[O:30])=[O:29].C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]([OH:27])([CH3:26])[CH2:23][CH2:24][O:25][S:28]([C:31]3[CH:37]=[CH:36][C:34]([CH3:35])=[CH:33][CH:32]=3)(=[O:30])=[O:29])=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 70873421HCID 70873421, compound

Product 1

HCID 86709367HCID 86709367, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-[4-(2,4-Dihydroxy-2-methylbutoxy)phenyl]piperazine-1-carboxylic acid tert-butyl ester (3.75 g, 9.9 mmol), tosyl chloride (2.07 g, 10.8 mmol), dichloromethane (38 ml) and triethylamine (2.75 ml, 19.7 mmol) were mixed and ice-cooled. 1,1,3,3,-Tetramethylpropanediamine (0.16 ml, 1.0 mmol) was added thereto and stirred at room temperature overnight. The reaction mixture was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. The organic layer was concentrated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→40:60) to afford the title compound as a colorless oil (4.69 g, 89%).

Workup

  1. temperatureice-cooled
  2. washThe reaction mixture was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over magnesium sulfate
  4. concentrationThe organic layer was concentrated
  5. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→40:60)

Sources & evidence

ORD record
ord-ad807f0d79434206a8417629b12c235f
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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