Triethylamine → HCID 18697984, compound

HRID 2289535Notes

Reaction equation

HRID 2289535 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([N:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1.C(N(CC)CC)C>C(O)C>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([S:16]([N:19]2[CH2:20][CH2:21][CH:22]([C:25]([N:27]3[CH2:28][CH2:29][N:30]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[N:7]=4)[CH2:31][CH2:32]3)=[O:26])[CH2:23][CH2:24]2)(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 18698044HCID 18698044, compound

Product 1

HCID 18697984HCID 18697984, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Methyl-4-chloro-pyrimidine (0.34 g) was added to a suspension of 1-(4-bromophenylsulphonyl)-4-(1-piperazinylcarbonyl)piperidine (1.0 g) in ethanol (10 ml) and 1(triethylamine (0.5 ml). The reaction was heated under reflux for 2 hours, cooled and the solvent removed by evaporation. The reaction mixture was purified by filtration column chromatography (silica, gradient elution dichloromethane to 10% methanol in dichloromethane) to give 1-(4-bromophenylsulphonyl)-4-[1-(2-methylpyrimidin-4-yl)piperazin-4-ylcarbonyl]piperidine as a solid (0.82 g) mpt 239-240° C.; NMR (CDCl3) 1.75-2.0 (m, 5H), 2.5 (m, 2H), 3.45-3.8 (m, 10H), 6.3 (m, 1H), 7.65 (m, 4H), 8.2 (m, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureunder reflux for 2 hours
  3. temperaturecooled
  4. customthe solvent removed by evaporation
  5. filtrationThe reaction mixture was purified by filtration column chromatography (silica, gradient elution dichloromethane to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-884ab4cd1db24b15b7cc250a0d8349d6
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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