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

HRID 1061053Notes

Reaction equation

HRID 1061053 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 saline 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 saline
  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-af7c3da4f76840f1b137362a6f0e24af
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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