Toluene → HCID 53828296, compound

HRID 374599Notes

Reaction equation

HRID 374599 reaction equation
[C:1]([C:4]1[C:5](=[O:19])[O:6][C:7]2[C:12]([CH:13]=1)=[CH:11][CH:10]=[C:9]([N:14]([CH2:17][CH3:18])[CH2:15][CH3:16])[CH:8]=2)(=[O:3])[CH3:2].[N:20]1([CH2:26][CH2:27][N:28]([CH2:37][CH3:38])[C:29]2[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.C([O-])(=O)C.[NH2+]1CCCCC1.C1(C)C=CC=CC=1>O>[CH2:15]([N:14]([CH2:17][CH3:18])[C:9]1[CH:8]=[C:7]2[C:12]([CH:13]=[C:4]([C:1](=[O:3])[CH:2]=[CH:33][C:32]3[CH:31]=[CH:30][C:29]([N:28]([CH2:37][CH3:38])[CH2:27][CH2:26][N:20]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]4)=[CH:36][CH:35]=3)[C:5](=[O:19])[O:6]2)=[CH:11][CH:10]=1)[CH3:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6887632H-1-Benzopyran-2-one, 3-acetyl-7-(diethylamino)-HCID 3014295Piperidinium acetateHCID 19438375HCID 19438375, compound

Product 1

HCID 53828296HCID 53828296, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-acetyl-7-diethylaminocoumarin (1.04 g, prepared according to the procedure described in U.S. Pat. No. 4,147,552), 1.20 g N-(2-piperidinoethyl)-N-ethyl-4-aminobenzaldehyde, 0.10 g piperidinium acetate, and 40 ml toluene were placed in a 100 ml round-bottomed flask fitted with a Dean-Stark trap and condenser. The solution was refluxed for 16 hr with removal of collected water. The toluene was evaporated under reduced pressure and a mixture of 20 ml water and 5 ml ethanol was added to the resultant viscous material. Upon stirring a solid precipitated which was isolated by filtration and drying to give 1.5 g of 7-diethylamino-3-(3-(N-ethyl-N-(2-piperidinoethyl)-4-aminophenyl)propenoyl)coumarin (4) as a red solid; λmax (ethanol)=475 nm. ##STR10##

Workup

  1. customfitted with a Dean-Stark trap and condenser
  2. customThe toluene was evaporated under reduced pressure
  3. additiona mixture of 20 ml water and 5 ml ethanol
  4. additionwas added to the resultant viscous material
  5. customprecipitated which
  6. customwas isolated by filtration
  7. customdrying

Sources & evidence

ORD record
ord-f5f0db41c7d64cb8bef7b21e4dea0fc2
Source dataset
uspto-grants-1996_01
Patent number
US05480994

Reaction notes

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