Piperidine → HCID 68561168, compound

HRID 19425Notes

Reaction equation

HRID 19425 reaction equation
[CH2:1]([N:3]([CH2:18][CH3:19])[C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=O)=[CH:7]1)[CH3:2].N1CCCCC1.[Cl-:26].[CH2:27]1[C:35]2[N+:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:29][CH2:28]1.C(OCC)(=O)C>C(O)(C)C>[Cl-:26].[CH2:1]([N:3]([CH2:18][CH3:19])[C:4](=[O:17])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([CH:15]=[C:27]2[C:35]3[N+:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH2:29][CH2:28]2)=[CH:7]1)[CH3:2]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 820167N,N-diethyl-2-(3-formyl-1H-indol-1-yl)acetamideHCID 685630602,3-dihydro-1H-indolizinium chloride

Product 1

HCID 68561168HCID 68561168, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

0.800 g of N,N-diethyl-2-(3-formyl-1H-indol-1-yl)acetamide was solubilized in 4.2 ml of isopropanol. 0.238 g of piperidine was added, followed by 0.435 g of 2,3-dihydro-1H-indolizinium chloride dissolved in 7 ml of isopropanol. The reaction mixtures were brought to 80° C. for 24 h, with stirring. 50 ml of ethyl acetate were added in order to precipitate the dye. The precipitate was filtered off, and washed with 3 times with 25 ml of ethyl acetate before being dried under vacuum until a constant weight was obtained. 1.09 g of orange powder were recovered. The analyses were in conformity with the expected structure.

Workup

  1. customThe reaction mixtures
  2. customto precipitate the dye
  3. filtrationThe precipitate was filtered off
  4. washwashed with 3 times with 25 ml of ethyl acetate
  5. custombefore being dried under vacuum until a constant weight
  6. customwas obtained
  7. custom1.09 g of orange powder were recovered

Sources & evidence

ORD record
ord-e3890998a6f74fe4bce322bc689e3077
Source dataset
uspto-grants-2010_06
Patent number
US07744658B2

Reaction notes

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