Diisopropylethylamine → HCID 66582712, compound

HRID 1972429Notes

Reaction equation

HRID 1972429 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6](Cl)(=[O:8])=[O:7].Cl.[CH2:11]([C@H:18]1[CH2:23][NH:22][CH2:21][CH2:20][NH:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:11]([C@@H:18]1[NH:19][CH2:20][CH2:21][N:22]([S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:8])=[O:7])[CH2:23]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 855182-Thiophenesulfonyl chlorideHCID 70655390HCID 70655390, compound

Product 1

HCID 66582712HCID 66582712, compoundYield 110.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Thiophenesulfonyl chloride (2.6 g, 14 mmol, Sigma-Aldrich, St. Louis, Mo.) was added to a stirring solution of (2S)-2-benzylpiperazine hydrochloride (4.5 g, 18 mmol), Hünig's base, (16 mL, 90 mmol), and CH2Cl2 (90 mL) at room temperature. After 3 h, silica gel (29 g) was added to the reaction mixture and the volatiles were removed in vacuo. The residue was subjected to column chromatography (120 g of silica, 2% MeOH in CH2Cl2) to give (3S)-3-benzyl-1-(2-thiophenylsulfonyl)piperazine (5.0 g) as a pale yellow solid.

Workup

  1. additionsilica gel (29 g) was added to the reaction mixture
  2. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-b78bedcd360d4b869adfe8fafde9c71d
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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