Triethylamine → Ave-9488

HRID 1876484Notes

Reaction equation

HRID 1876484 reaction equation
Cl.[NH2:2][CH:3]1[CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4]1.C(N(CC)CC)C.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>O1CCCC1>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([NH:2][CH:3]2[CH2:11][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:4]2)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 1227642-Aminoindan hydrochloride

Product 1

HCID 10131276Ave-9488

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

43.70 g (258 mmol) of 2-aminoindane hydrochloride and 53.43 g (528 mmol) of triethylamine were added to 250 ml of tetrahydrofuran, 42.89 g (270 mmol) of 4-fluorobenzoyl chloride were added, and the mixture was stirred for 2 hours at room temperature. The resulting mixture was then poured onto an ice/HCl mixture, the obtained precipitate was filtered, washed with a NaHCO3 solution and water and dried in vacuo. The crude product was crystallized from methanol. Yield: 47.8 g (73%) of a white crystalline product.

Workup

  1. additionwere added
  2. filtrationthe obtained precipitate was filtered
  3. washwashed with a NaHCO3 solution and water
  4. customdried in vacuo
  5. customThe crude product was crystallized from methanol

Sources & evidence

ORD record
ord-4efe17457efc4158b575d8d6709e1489
Source dataset
uspto-grants-2012_11
Patent number
US08309608B2

Reaction notes

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