Hydrochloric Acid → HCID 22185245, compound

A mixture of 4-isopropylphenylhydrazine hydrochloride (660 mg, 3.55 mmol) and 4-phthalimidobutanal diethyl acetal (1.15 g, 3.95 mmol) in Ethanol (EtOH; 30 ml) was heated at 60° C. to 65° C. for 1 h with water (0.050 ml). The mixture was then treated with concentrated HCl (0.50 ml) and refluxed for 14 h. After concentrating the reaction, the residue was partioned in methylene chloride and saturated aqueous NaHCO3. The aqueous solution was extracted with methylene chloride (3 times) and the combined organic solutions were dried (MgSO4) and concentrated to give after chromatography (4:1 hexane-ethyl acetate) on silica gel 146 mg of product. The above product was treated with hydrazine hydrate (1 ml) in EtOH (4 ml) and water (1 ml) and stirred at RT overnight. After concentrating the reaction to an aqueous mixture, the product was extracted with methylene chloride (3 times). The combined organic solution was dried (MgSO4) and concentrated. The residue was redissolved in methylene chloride and treated with 1M HCl in ether. The precipitate was collected and washed with ether and hexane and dried to provide 102 mg of 6-isopropyltryptamine hydrochloride salt. This tryptamine obtained above was transformed into 7-isopropyl-β-carboline according to the procedure used in example 3. The hydrochloride salt was obtained by treating a solution of 7-Isopropyl-β-carboline in methylene chloride with 1M HCl in ether and concentrating. The residue was triturated with (1:1) methylene chloride-hexane to give 15 mg of 7-isopropyl-β-carboline hydrochloride.

1. temperaturerefluxed for 14 h
2. concentrationAfter concentrating
3. customthe reaction
4. extractionThe aqueous solution was extracted with methylene chloride (3 times)
5. dry with materialthe combined organic solutions were dried (MgSO4)
6. concentrationconcentrated
7. customto give after chromatography (4:1 hexane-ethyl acetate) on silica gel 146 mg of product
8. concentrationAfter concentrating
9. customthe reaction to an aqueous mixture
10. extractionthe product was extracted with methylene chloride (3 times)
11. dry with materialThe combined organic solution was dried (MgSO4)
12. concentrationconcentrated
13. dissolutionThe residue was redissolved in methylene chloride
14. additiontreated with 1M HCl in ether
15. customThe precipitate was collected
16. washwashed with ether and hexane
17. customdried

ORD record

ord-ae44eb11194440369cabeeff2c235a58

Source dataset

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07026331B2