Hydrochloric Acid → (RS)-1-(7-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-propylamine hydrochloride

HRID 2303952Notes

Reaction equation

HRID 2303952 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH2:19][C:12]3=[C:11]([CH:20]=[C:21]([N+:23]([O-])=O)[CH3:22])[C:10]=2[CH:9]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+].Cl>C1COCC1>[ClH:7].[Cl:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH2:19][C:12]3=[C:11]([CH2:20][CH:21]([NH2:23])[CH3:22])[C:10]=2[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 698492581-(7-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propene

Product 1

HCID 18462123(RS)-1-(7-Chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-propylamine hydrochlorideYield 89.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of lithium aluminium hydride (1.0 M in THF, 2.7 mL, 2.7 mmol) in added THF (5 mL) under argon was added dropwise a solution of 1-(7-chloro-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propene (0.5 g, 1.8 mmol) in THF (10 mL). The mixture was heated under reflux for 4 h and cooled to 0° C. To the mixture was added dropwise aqueous potassium sodium tartrate solution (50 mL) and the mixture was stirred for 30 min and filtered through kieselguhr. The filtrate was extracted with dichloromethane (3×30 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate), concentrated in vacuo, treated with ethereal hydrogen chloride (1.0 M, 2 mL, 2 mmol) and concentrated in vacuo. The concentrate was recrystallised (2-propanol) to give the title compound as a white solid (0.23 g, 45%): mp 272-273° C.; Found: C, 57.86; H, 6.37; N, 9.41%. C14H17ClN2.HCl. 0.25H2O requires: C, 58.03; H, 6.39; N, 9.67%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 4 h
  3. filtrationfiltered through kieselguhr
  4. extractionThe filtrate was extracted with dichloromethane (3×30 mL)
  5. washThe combined organic extracts were washed (water, brine)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. concentrationconcentrated in vacuo
  9. customThe concentrate was recrystallised (2-propanol)

Sources & evidence

ORD record
ord-eedf954a1abd47afb8f387a4acff8cd9
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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