tert-Butyl piperazine-1-carboxylate → HCID 22467481, compound

HRID 1934732Notes

Reaction equation

HRID 1934732 reaction equation
Cl[S:2]([C:5]1[CH:6]=[CH:7][C:8]([F:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[N:15]1([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1>ClCCl>[C:24]([O:23][C:21]([N:15]1[CH2:20][CH2:19][N:18]([S:2]([C:5]2[CH:6]=[CH:7][C:8]([F:14])=[C:9]([CH:13]=2)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3])[CH2:17][CH2:16]1)=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 6089842-Fluoro-5-chlorosulfonylbenzoic acid

Product 1

HCID 22467481HCID 22467481, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-Chlorosulfonyl-2-fluorobenzoic acid (2 g) was dissolved in dichloromethane (20 mL) under nitrogen atmosphere and cooled to 0° C. tert-Butyl 1-piperazinecarboxylate (3.12 g) was added portionwise to the solution at 0° C. and stirred for 3 hours at ambient temperature. The organic solvent was evaporated in vacuo, and the residue was dissolved in 1N-sodium hydroxide solution. The aqueous solution was washed with diethyl ether and acidified with 1N-hydrochloric acid. The precipitates were collected by filtration and washed with water to give 5-[4-(tert-butoxycarbonyl)piperazin-1-ylsulfonyl]-2-fluorobenzoic acid (2.26 g) as a colorless solid substance.

Workup

  1. additionwas added portionwise to the solution at 0° C.
  2. customThe organic solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in 1N-sodium hydroxide solution
  4. washThe aqueous solution was washed with diethyl ether
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-2eb25892942849d8a8116fad9ed8c904
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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