Triethylamine → HCID 54249792, compound

HRID 1249725Notes

Reaction equation

HRID 1249725 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.Cl.Cl.Cl.[CH3:18][C:19]1[N:24]=[C:23]([N:25]2[CH2:30][CH2:29][CH:28]([CH2:31][N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[CH2:27][CH2:26]2)[CH:22]=[CH:21][N:20]=1.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]([F:14])([F:13])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:35]2[CH2:34][CH2:33][N:32]([CH2:31][CH:28]3[CH2:29][CH2:30][N:25]([C:23]4[CH:22]=[CH:21][N:20]=[C:19]([CH3:18])[N:24]=4)[CH2:26][CH2:27]3)[CH2:37][CH2:36]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 70154464HCID 70154464, compound

Product 1

HCID 54249792HCID 54249792, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-trifluoromethylphenylsulphonylchloride (367 mg) in methylene chloride (5 ml) was added dropwise over 5 minutes to a mixture of 4-[1-(2-methylpyrimidin-4-yl)-4-piperidylmethyl]piperazine trihydrochloride (625 mg) and triethylamine (1.04 ml) in dichloromethane (20 ml) at 0° C. The solution was stirred at ambient temperature for 18 hours. The solution was diluted with dichloromethane and washed with water, dried (Na2SO4) and evaporated. The residue was purified by chromatography eluting with 1-2% methanol in dichloromethane. Filtration from ether gave 1-(4-trifluoromethylphenylsulphonyl)-4-[1-(2-methylpyrimidin-4-yl)-4-piperidyimethyl]piperazine (358 mg), as a solid, mp 135-136° C.

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by chromatography
  5. washeluting with 1-2% methanol in dichloromethane
  6. filtrationFiltration from ether

Sources & evidence

ORD record
ord-07472df723824fa78e78a31482b10528
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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