Hydrochloric Acid → HCID 22185251, compound

HRID 1168717Notes

Reaction equation

HRID 1168717 reaction equation
[CH:1]([C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=3[NH:14]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[ClH:17]>C(Cl)Cl.CCOCC>[ClH:17].[CH:1]([C:4]1[CH:16]=[C:15]2[C:7]([C:8]3[CH:9]=[CH:10][N:11]=[CH:12][C:13]=3[NH:14]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 22185249HCID 22185249, compound

Product 1

HCID 22185251HCID 22185251, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. concentrationconcentrating
  2. customThe residue was triturated with (1:1) methylene chloride-hexane

Sources & evidence

ORD record
ord-891e0ecd957045d7866978d4fab54391
Source dataset
uspto-grants-2003_09
Patent number
US06627637B2

Reaction notes

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