Triethylamine → HCID 67071626, compound

HRID 2263905Notes

Reaction equation

HRID 2263905 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[Cl:24][CH2:25][CH2:26][CH2:27][S:28](Cl)(=[O:30])=[O:29]>O1CCCC1>[C:4]([O:3][C:1]([N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][NH:16][S:28]([CH2:27][CH2:26][CH2:25][Cl:24])(=[O:30])=[O:29])[CH2:12][CH2:13]1)=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 1514400tert-Butyl 4-(2-aminoethyl)piperazine-1-carboxylate

Product 1

HCID 67071626HCID 67071626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-Boc-4-(2-aminoethyl)-piperazine (1.26 g, 6.8 mmol, Aldrich) and triethylamine (1 mL) in tetrahydrofuran (10 mL), 3-chloro-propylsulfonyl chloride (0.68 mL, 6.94 mmol, Aldrich) was added slowly at room temperature. The mixture was stirred for 30 min at room temperature and the reaction was quenched with water. It was extracted with ethyl acetate and the extracts were combined and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo to give 4-[2-(3-chloro-propane-1-sulfonylamino)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester. It was taken in tetrahydrofuran (20 mL), and cesium carbonate (500 mg) sodium iodide (80 mg) were added and the mixture was stirred at reflux overnight. The mixture was cooled to room temperature and poured into water. It was extracted with ethyl acetate (3×15 mL), and the extracts were combined and dried over anhydrous sodium sulfate. The solids were filtered off, and the filtrate was concentrated in vacuo to give 2.01 g of 4-[2-(1,1-dioxo-isothiazolidine-2-yl)-ethyl]-piperazine-1-carboxylic acid tert-butyl ester as a solid. LR-MS: 334 [(M+H)+]

Workup

  1. customthe reaction was quenched with water
  2. extractionIt was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe solids were filtered off
  5. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-49bd3d15e5db48099bb7901b5d055623
Source dataset
uspto-grants-2010_12
Patent number
US07851626B2

Reaction notes

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