Triethylamine → HCID 18328909, compound

HRID 1249732Notes

Reaction equation

HRID 1249732 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[CH3:12][C:13]1[N:18]=[C:17]([N:19]2[CH2:24][CH2:23][C:22]([C:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[O:27])([OH:25])[CH2:21][CH2:20]2)[CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([N:31]2[CH2:32][CH2:33][N:28]([C:26]([C:22]3([OH:25])[CH2:21][CH2:20][N:19]([C:17]4[CH:16]=[CH:15][N:14]=[C:13]([CH3:12])[N:18]=4)[CH2:24][CH2:23]3)=[O:27])[CH2:29][CH2:30]2)=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 685154-Bromobenzoyl chlorideHCID 18328915HCID 18328915, compound

Product 1

HCID 18328909HCID 18328909, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromobenzoylchloride (0.53 g) in dichloromethane (3 ml) was added to a mixture of 1-(2-methylpyrimidin-4-yl)-4-(piperazin-1-ylcarbonyl)piperidine-4-ol hydrochloride (0.65 g) and triethylamine (1.7 ml) in dichloromethane (30 ml) at 5° C. The solution was stirred at ambient temperature for 18 hours. The resulting solution was evaporated to dryness. The residue was dissolved in dichloromethane and the solution was washed with water, dried (Na2SO4) and evaporated to dryness. The residue was purified by flash column chromatography on alumina (ICN alumina N32-63), using 0.1-0.4% methanol in dichloromethane as eluent. Recrystallisation from ethyl acetate/isohexane gave 1-(4-bromobenzoyl)-4-[1-(2-methylpyrimidin-4-yl)-4-hydroxy-4-piperidylcarbonyl]piperazine, as a colourless solid (0.53 g), mp114-117° C.

Workup

  1. customThe resulting solution was evaporated to dryness
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washthe solution was washed with water
  4. dry with materialdried (Na2SO4)
  5. customevaporated to dryness
  6. customThe residue was purified by flash column chromatography on alumina (ICN alumina N32-63)
  7. customRecrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-cc19093d099242279c8e16779c3a4b80
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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