Triethylamine → 1-(Tert-butoxycarbonyl)-4-[2-(4-chlorophenyl)ethynesulfonyl]piperazine

HRID 278578Notes

Reaction equation

HRID 278578 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH2:17][C:18](=O)[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)(=[O:15])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 226282031-(tert-Butoxycarbonyl)-4-(4-chlorobenzoylmethanesulfonyl)piperazine

Product 1

HCID 226280621-(Tert-butoxycarbonyl)-4-[2-(4-chlorophenyl)ethynesulfonyl]piperazineYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(tert-butoxycarbonyl)-4-(4-chlorobenzoylmethanesulfonyl)piperazine (640 mg) and 2-chloro-1-methylpyridinium iodide (650 mg) in dichloromethane (8 ml) was added dropwise triethylamine (4 ml) at 0° C., and the mixture was stirred at room temperature for 24 hours. The reaction solution was concentrated and purified with silica gel column chromatography (hexane/ethyl acetate=2/1) to give a colorless solid of 1-(tert-butoxycarbonyl)-4-[2-(4-chlorophenyl)ethynesulfonyl]piperazine (521 mg).

Workup

  1. concentrationThe reaction solution was concentrated
  2. custompurified with silica gel column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-84264b35882840db9a9b27b6847ce0f4
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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