Triethylamine → HCID 18698014, compound

HRID 2289543Notes

Reaction equation

HRID 2289543 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)=[O:19])[CH2:14][CH2:13]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:26][C:27]1[N:32]=[C:31](Cl)[CH:30]=[CH:29][N:28]=1.C(N(CC)CC)C>C(O)C>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:13][CH2:14][CH:15]([C:18]([N:20]3[CH2:21][CH2:22][N:23]([C:29]4[CH:30]=[CH:31][N:32]=[C:27]([CH3:26])[N:28]=4)[CH2:24][CH2:25]3)=[O:19])[CH2:16][CH2:17]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4244474-Chloro-2-methylpyrimidineHCID 18697997HCID 18697997, compound

Product 1

HCID 18698014HCID 18698014, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude 1-(4-chlorophenylsulphonyl)-4-(piperazin-4-ylcarbonyl)piperidine hydrochloride, 2-methyl-4-chloro-pyrimidine (299 mg) and triethylamine (1.47 ml) were heated under reflux in ethanol (12 ml) for 5 hours. The solvent was removed by evaporation. Purification by filtration column chromatography (silica) eluting with 2% methanol/dichloromethane increasing to 10% methanol/dichloromethane gave 1-(4-chlorophenylsulphonyl)-4-[1-(2-methylpyrimidin-4-yl)piperazin-4-ylcarbonyl]piperidine as a solid (0.87 g); NMR (CDCl3): 1.7-2.0 (m, 5H), 2.5 (m, 5H), 3.5-3.8 (m, 10H), 6.3 (m, 1H), 7.5 (m, 2H), 7.7 (m, 2H), 8.2 (m, 1H).

Workup

  1. customThe solvent was removed by evaporation
  2. customPurification
  3. filtrationby filtration column chromatography (silica)
  4. washeluting with 2% methanol/dichloromethane increasing to 10% methanol/dichloromethane

Sources & evidence

ORD record
ord-aa0f485fca464fed9d1375adb41dcab7
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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