4-Methylmorpholine → 2,5-dimethyl-N-(1,1-dimethylindan-4-yl)3-furan carboxamide

HRID 2072673Notes

Reaction equation

HRID 2072673 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([NH2:11])[C:5]=2[CH2:4][CH2:3]1.CN1CCOCC1.[CH3:20][C:21]1[O:22][C:23]([CH3:29])=[CH:24][C:25]=1[C:26](Cl)=[O:27]>CCOCC>[CH3:20][C:21]1[O:22][C:23]([CH3:29])=[CH:24][C:25]=1[C:26]([NH:11][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]2([CH3:12])[CH3:1])=[O:27]

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 27348042,5-Dimethyl-3-furoyl ChlorideHCID 131156151,1-Dimethyl-2,3-dihydro-1H-inden-4-amine

Product 1

HCID 140541092,5-dimethyl-N-(1,1-dimethylindan-4-yl)3-furan carboxamideYield 86.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 15 ml of an ether solution of 1.5 g (8.57 mmols) of 1,1-dimethylindane-4-amine, 2 ml of N-methyl morpholine and 1.4 g (8.83 mmols) of 2,5-dimethyl-3-furan carboxylic acid chloride were added under cooling. The mixture was stirred at room temperature for 1 hour and then washed sequentially with water and brine. The solution was dried with magnesium sulfate. The resultant concentrate was purified with silica gel column chromatography (solvent for elution; ethyl acetate/n-hexane=1/4), thereby obtaining 2.1 g of light yellow crystals (Compound No. 20 shown in Table 6). The yield was 85.8%.

Workup

  1. temperatureunder cooling
  2. washwashed sequentially with water and brine
  3. dry with materialThe solution was dried with magnesium sulfate
  4. concentrationThe resultant concentrate
  5. customwas purified with silica gel column chromatography (solvent for elution; ethyl acetate/n-hexane=1/4)

Sources & evidence

ORD record
ord-d7dd0303eec3497db96408ae672c5b02
Source dataset
uspto-grants-1990_04
Patent number
US04914097

Reaction notes

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