Triethylamine → 4-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

HRID 352764Notes

Reaction equation

HRID 352764 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[Cl:21][CH2:22][CH2:23][CH2:24][S:25](Cl)(=[O:27])=[O:26]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:25]([CH2:24][CH2:23][CH2:22][Cl:21])(=[O:27])=[O:26])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 154103-Chloropropanesulphonyl chlorideHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 227098904-tert-Butoxycarbonyl-1-[(3-chloro-1-propyl)sulfonyl]piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Under an argon gas atmosphere, 1-tert-butoxycarbonylpiperazine (3.00 g) and triethylamine (2.24 ml) were dissolved in dichloromethane (40 ml) under ice cooling, followed by the addition of 3-chloro-1-propanesulfonic acid chloride (1.96 g). The resulting mixture was stirred for 20 minutes under ice cooling and then, at room temperature for 10 minutes. The reaction mixture was diluted with dichloromethane, washed with water and saturated aqueous NaCl solution and then dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of ethyl acetate and hexane, whereby the title compound (4.36 g, 83%) was obtained.

Workup

  1. waitat room temperature for 10 minutes
  2. washwashed with water and saturated aqueous NaCl solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. customThe residue was recrystallized from a mixed solvent of ethyl acetate and hexane, whereby the title compound (4.36 g, 83%)
  6. customwas obtained

Sources & evidence

ORD record
ord-8a4758ad4876444aa58be1d0327076c3
Source dataset
uspto-grants-2004_06
Patent number
US06747023B1

Reaction notes

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