Hydrochloric Acid → HCID 118162198, compound

HRID 1749534

Reaction equation

HRID 1749534 reaction equation
[ClH:1].[F:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:12][CH2:13][NH2:14])=[CH:8][NH:9]2)=[CH:5][CH:4]=1.Cl.CS(C)=[O:18]>>[ClH:1].[NH2:14][CH2:13][CH2:12][CH:7]1[C:6]2[C:10](=[CH:11][C:3]([F:2])=[CH:4][CH:5]=2)[NH:9][C:8]1=[O:18]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 30850786-Fluoro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 118162198HCID 118162198, compoundYield 47%

Conditions

Temperature
50 °C

Procedure

To a solution of 2-(6-fluoro-1H-indol-3-yl)ethanamine hydrochloride (500 mg, 2.3 mmol) in DMSO (0.8 mL) was added hydrochloric acid (36%, 1.3 g, 12.8 mmol). The resulting reaction mixture was stirred at 50° C. in a sealed tube for 6 h. After cooling to room temperature, the reaction mixture was filtered. The resulting cake was stirred in EtOH (5 mL). The mixture was filtered and dried to give the desired product (250 mg, 1.28 mmol, 47% yield) as a yellow solid. MS (ESI) m/z 195.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered
  4. stirringThe resulting cake was stirred in EtOH (5 mL)
  5. filtrationThe mixture was filtered
  6. customdried

Sources & evidence

ORD record
ord-02d7faa9def14b0a8852b78dc2eb5fce
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Linked notes

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