Propanal → HCID 18348172, compound

HRID 2267962Notes

Reaction equation

HRID 2267962 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[CH:21](=O)[CH2:22][CH3:23].[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1.[OH-].[Na+]>O1CCOCC1.C(O)(=O)C.C(OCC)C>[NH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH:21]([N:12]2[CH2:11][CH2:10][N:9]([CH:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:14][CH2:13]2)[CH2:22][CH3:23])=[CH:26]1

Participants

8

Reactant 4

HCID 527PropanalHCID 798IndoleHCID 9340NorchlorcyclizineHCID 14798Sodium Hydroxide

Product 1

HCID 18348172HCID 18348172, compoundYield 11.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2.0 grams (0.006 mole) of N-[(4-chlorophenyl)(phenyl)-methyl]piperazine and 0.5 mL (0.007 mole) of propionaldehyde in 8.0 mL of dioxane and 8.0 mL of glacial acetic acid was stirred and cooled in an ice bath. To this a solution of 0.7 gram (0.006 mole) of indole in 10.0 mL of dioxane was added dropwise during a 15 minute period. Upon completion of the addition the reaction mixture was allowed to warm to ambient temperature, where it stirred for about 18 hours, after which the reaction mixture was poured into a mixture of diethyl ether and aqueous 5% sodium hydroxide. The ether layer was separated and washed with water and then with an aqueous saturated sodium chloride solution. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to an oil, which was subjected to column chromatography on silica gel. Elution was accomplished with pure hexane, followed by diethyl ether/hexane mixtures and then pure diethyl ether. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.3 gram of N-[1-(indol-3yl)propyl]-N′-[(4chlorophenyl)-(phenyl)methyl]piperazine. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperaturecooled in an ice bath
  2. additionUpon completion of the addition the reaction mixture
  3. customThe ether layer was separated
  4. washwashed with water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to an oil, which
  8. washElution
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-188b07c3820649b1b9a0f8e147662775
Source dataset
uspto-grants-2001_12
Patent number
USH0002007H1

Reaction notes

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