Triethylamine → HCID 54121165, compound

HRID 1249727Notes

Reaction equation

HRID 1249727 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.Cl.Cl.[CH3:14][C:15]1[N:20]=[C:19]([N:21]2[CH2:26][CH2:25][CH:24]([CH2:27][N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH2:23][CH2:22]2)[CH:18]=[CH:17][N:16]=1.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:31]2[CH2:30][CH2:29][N:28]([CH2:27][CH:24]3[CH2:25][CH2:26][N:21]([C:19]4[CH:18]=[CH:17][N:16]=[C:15]([CH3:14])[N:20]=4)[CH2:22][CH2:23]3)[CH2:33][CH2:32]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 70154464HCID 70154464, compound

Product 1

HCID 54121165HCID 54121165, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of 4-fluorobenzoyl chloride(238 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-fluorobenzoyl)-4-[1-(2-methyl-4-pyrimidinyl)-4-piperidylmethyl]piperazine, as a solid (244 mg), mp 127-128° 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-d13b0a89194842568a15525b903e74e3
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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