Formaldehyde → N-(4-chloroindol-3-ylmethyl)-N'-[(4-chlorophenyl)(2-chlorophenyl)methyl]piperazine

HRID 2267959Notes

Reaction equation

HRID 2267959 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1)[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C=O.[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[CH:27]=[CH:28][NH:29]2.[C:34](=O)(O)[O-].[Na+]>O1CCOCC1.C(O)(=O)C>[Cl:24][C:25]1[CH:33]=[CH:32][CH:31]=[C:30]2[C:26]=1[C:27]([CH2:34][N:12]1[CH2:11][CH2:10][N:9]([CH:8]([C:15]3[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=3)[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH2:14][CH2:13]1)=[CH:28][NH:29]2

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 913454-ChloroindoleHCID 516892Sodium BicarbonateHCID 5181446n'-[(2-Chlorophenyl)(4-chlorophenyl)methyl]piperazine

Product 1

HCID 18348178N-(4-chloroindol-3-ylmethyl)-N'-[(4-chlorophenyl)(2-chlorophenyl)methyl]piperazine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A stirred solution of 0.4 gram (0.001 mole) of N′-[(2-chlorophenyl)(4-chlorophenyl)methyl]piperazine in 1 mL of dioxane was cooled to 0° C. To this was added 2 mL of glacial acetic acid followed by 0.14 mL of 37% aqueous formaldehyde. A solution of 0.2 gram (0.001 mole) of 4-chloroindole in 1 mL of dioxane was then slowly added. Upon completion of the addition the reaction mixture was warmed to ambient temperature where it stirred for five hours. The reaction mixture was then cooled to 0° C., neutralized with aqueous saturated sodium bicarbonate solution, and extracted with two portions of diethyl ether. The combined extracts were washed with an aqueous saturated sodium chloride solution and dried with sodium sulfate, yielding 0.6 gram of crude material. The crude material was purified by preparative TLC. Elution was accomplished with 3:2 ethyl acetate: methylene chloride. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.4 gram of N-(4-chloroindol-3-ylmethyl)-N′-[(4-chlorophenyl)(2-chlorophenyl)methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction mixture
  2. temperatureThe reaction mixture was then cooled to 0° C.
  3. extractionextracted with two portions of diethyl ether
  4. washThe combined extracts were washed with an aqueous saturated sodium chloride solution
  5. dry with materialdried with sodium sulfate
  6. customyielding 0.6 gram of crude material
  7. customThe crude material was purified by preparative TLC
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0b91df781f044c9d9a466376161279e5
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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