Hydrochloric Acid → HCID 18462124, compound

HRID 2303953Notes

Reaction equation

HRID 2303953 reaction equation
[F:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[C:6]([CH:14]=[C:15]([N+:17]([O-])=O)[CH3:16])=[C:7]3[CH2:13][CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].[ClH:33]>C(OCC)C>[ClH:33].[F:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[C:6]([CH2:14][CH:15]([NH2:17])[CH3:16])=[C:7]3[CH2:13][CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9855836Potassium sodium tartarateHCID 69849107HCID 69849107, compound

Product 1

HCID 18462124HCID 18462124, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

(RS)-1-(6,7-Difluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-propylamine hydrochloride was prepared from 1-(6,7-difluoro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propene according to the method described in Example 1 with the following modifications: the reaction mixture was heated under reflux for 4 h, cooled to 0° C. and poured into aqueous potassium sodium tartrate solution (150 mL) and diethyl ether (100 mL). The mixture was stirred for 30 min, filtered through celite® and the filtrate was extracted with ethyl acetate (2×50 mL). The combined organic extracts were washed (brine), dried (magnesium sulfate), concentrated in vacuo, treated with ethereal hydrogen chloride (1.0 M, 2 mL, 2 mmol) and concentrated in vacuo. The residue was recrystallised (ethyl acetate, 2-propanol) to give the title compound as a white solid (0.55 g, 63%): mp 264-266° C. Found: C, 58.67; H, 6.09; N, 9.65%. C14H16F2N2.HCl requires: C, 58.64; H, 5.98; N, 9.76%.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. filtrationfiltered through celite®
  4. extractionthe filtrate was extracted with ethyl acetate (2×50 mL)
  5. washThe combined organic extracts were washed (brine)
  6. dry with materialdried (magnesium sulfate)
  7. concentrationconcentrated in vacuo
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallised (ethyl acetate, 2-propanol)

Sources & evidence

ORD record
ord-94f28fd6fcd448dd9848194e806470c0
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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