Triethylamine → 1-(6-Chloronaphth-2-ylsulphonyl)-4-[1-[4-pyrimidinyl]piperidin-4-ylcarbonyl]piperazine

HRID 2288727Notes

Reaction equation

HRID 2288727 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([S:26]([N:29]1[CH2:34][CH2:33][N:32]([C:35]([CH:37]3[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]3)=[O:36])[CH2:31][CH2:30]1)(=[O:28])=[O:27])[CH:20]=[CH:19]2>C(O)C>[Cl:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH:22]=[C:21]([S:26]([N:29]1[CH2:30][CH2:31][N:32]([C:35]([CH:37]3[CH2:42][CH2:41][N:40]([C:2]4[CH:7]=[CH:6][N:5]=[CH:4][N:3]=4)[CH2:39][CH2:38]3)=[O:36])[CH2:33][CH2:34]1)(=[O:27])=[O:28])[CH:20]=[CH:19]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6428344-ChloropyrimidineHCID 121120194-(1-(6-Chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine

Product 1

HCID 227218941-(6-Chloronaphth-2-ylsulphonyl)-4-[1-[4-pyrimidinyl]piperidin-4-ylcarbonyl]piperazineYield 60.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloropyrimidine (1.72 g) and triethylamine (5.3 ml) were added to a solution of 4-(1-(6-chloronaphth-2-ylsulphonyl)piperazin-4-ylcarbonyl)piperidine (4 g) in ethanol (100 ml) and the mixture heated on a steam bath overnight. The mixture was cooled to give a precipitate which was collected to filtration and recrystallised from acetonitrile to give 1-(6-chloronaphth-2-ylsulphonyl)-4-[1-[4-pyrimidinyl]piperidin-4-ylcarbonyl]piperazine (2.88 g); mp 218-219° C.;

Workup

  1. temperaturethe mixture heated on a steam bath overnight
  2. temperatureThe mixture was cooled
  3. customto give a precipitate which
  4. filtrationwas collected to filtration
  5. customrecrystallised from acetonitrile

Sources & evidence

ORD record
ord-0ef9829a6daf449fa846376e6f08802e
Source dataset
uspto-grants-2000_07
Patent number
US06090813

Reaction notes

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