Triethylamine → 3-(1-methylethyl)-4-(((2S)-4-(2-thiophenylsulfonyl)-2-piperazinyl)methyl)-2-piperazinone

HRID 1972565Notes

Reaction equation

HRID 1972565 reaction equation
[CH3:1][CH:2]([CH:4]1[N:9]([CH2:10][C@H:11]2[CH2:16][NH:15][CH2:14][CH2:13][NH:12]2)[CH2:8][CH2:7][NH:6][C:5]1=[O:17])[CH3:3].C(N(CC)CC)C.[S:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[S:30](Cl)(=[O:32])=[O:31]>ClCCl>[CH3:3][CH:2]([CH:4]1[N:9]([CH2:10][C@H:11]2[CH2:16][N:15]([S:30]([C:26]3[S:25][CH:29]=[CH:28][CH:27]=3)(=[O:32])=[O:31])[CH2:14][CH2:13][NH:12]2)[CH2:8][CH2:7][NH:6][C:5]1=[O:17])[CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 665825553-(1-methylethyl)-4-((2R)-2-piperazinylmethyl)-2-piperazinone

Product 1

HCID 665829463-(1-methylethyl)-4-(((2S)-4-(2-thiophenylsulfonyl)-2-piperazinyl)methyl)-2-piperazinoneYield 93.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3-(1-methylethyl)-4-((2R)-2-piperazinylmethyl)-2-piperazinone (0.161 g, 0.670 mmol, Example 184) and triethylamine (0.290 mL, 2.083 mmol) in dichloromethane (5.82 mL) was added a solution of 2-thiophenesulfonyl chloride (0.138 g, 0.756 mmol, Sigma-Aldrich, St. Louis, Mo.) in CH2Cl2 (1 mL) drop-wise at room temperature. The solution was stirred for 30 min and then the mixture was concentrated. The residue was re-dissolved in CH2Cl2 and washed with water followed by brine. The organic layer was dried (Na2SO4), filtered, and concentrated to give 3-(1-methylethyl)-4-(((2S)-4-(2-thiophenylsulfonyl)-2-piperazinyl)methyl)-2-piperazinone (242 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. dissolutionThe residue was re-dissolved in CH2Cl2
  3. washwashed with water
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-41421599711a432cadc3b6cfdb14c9bf
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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