Triethylamine → N-(2-n-Propylpentanoyl)-1-aminoindan

HRID 1418083Notes

Reaction equation

HRID 1418083 reaction equation
[C:1](Cl)(=[O:9])[CH:2]([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][CH3:5].[NH2:11][CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.CCN(CC)CC.CCOC(C)=O>C1(C)C=CC=CC=1.O>[CH2:3]([CH:2]([CH2:6][CH2:7][CH3:8])[C:1]([NH:11][CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=[O:9])[CH2:4][CH3:5]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 762402-Propylvaleryl chlorideHCID 123445(+-)-1-Aminoindan

Product 1

HCID 11658951N-(2-n-Propylpentanoyl)-1-aminoindanYield 69.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A solution of valproyl chloride (1.55 g, 9.6 mmole) in toluene (25 ml) was added dropwise to a stirred and ice-cooled solution of 1-aminoindan (1.47 g, 10.0 mmole) and Et3N (1.11 g, 11 mmole). The mixture was stirred at ambient temperature for 17 hours, EtOAc (60 ml) and water (50 ml) were added and the phases were separated. The organic phase was washed successively with 0.1N HCl (40 ml), 0.1N NaHCO3 (40 ml) and saturated NaCl (40 ml), dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue was treated with hexane (15 ml, 30 min stirring, RT) and filtered. The crude product was crystallized from hexane: EtOAc (70:30 mixture), to give 1.72 g (6.65 mmole, 69%) of a white crystalline solid, mpt: 133°-4° C.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 17 hours
  2. customthe phases were separated
  3. washThe organic phase was washed successively with 0.1N HCl (40 ml), 0.1N NaHCO3 (40 ml) and saturated NaCl (40 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. additionThe residue was treated with hexane (15 ml, 30 min stirring, RT)
  7. filtrationfiltered
  8. customThe crude product was crystallized from hexane: EtOAc (70:30 mixture)

Sources & evidence

ORD record
ord-196527a55c554144914a0741d108a1c7
Source dataset
uspto-grants-1999_03
Patent number
US05880159

Reaction notes

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