Triethylamine → N-(2,3-Dihydro-1H-inden-1-yl)butanamide

HRID 1860306Notes

Reaction equation

HRID 1860306 reaction equation
[C:1](Cl)(=[O:5])[CH2:2][CH2:3][CH3:4].[NH2:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1.CCN(CC)CC>COCCOC>[C:1]([NH:7][CH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9]1)(=[O:5])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 123445(+-)-1-Aminoindan

Product 1

HCID 18627825N-(2,3-Dihydro-1H-inden-1-yl)butanamideYield 58%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of butyryl chloride (5.33 g, 50 mmole) in anh. DME (60 ml) was added slowly to a stirred and ice-cooled solution of 1-aminoindan (6.66 g, 50 mmole) and Et3N (10.0 g, 100 mmole) in anh. DME (75 ml), and the mixture stirred at ambient temperature for 24 hr. After removal of volatiles under reduced pressure, the residue was taken up in 1:1 water/EtOAc mixture (300 ml). The organic layer was separated, dried on Na2SO4 and evaporated to dryness. The crude product was crystallized from EtOAc, to give 5.9 g (58%) of the title compound as a white solid, m.p.: 84°-5° C.

Workup

  1. stirringthe mixture stirred at ambient temperature for 24 hr
  2. customAfter removal of volatiles under reduced pressure
  3. customThe organic layer was separated
  4. customdried on Na2SO4
  5. customevaporated to dryness
  6. customThe crude product was crystallized from EtOAc

Sources & evidence

ORD record
ord-395ed7d43f2c40a89dd76cfb7d894494
Source dataset
uspto-grants-2003_03
Patent number
US06528685B2

Reaction notes

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