Hydrochloric Acid → 2-[3-(2-Fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine hydrochloride

HRID 6956

Reaction equation

HRID 6956 reaction equation
O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([C:28]1[C:36]2[C:31](=[C:32]([O:37][CH2:38][CH2:39][NH2:40])[CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)(=[O:27])=[O:26].[ClH:41]>C(O)C>[ClH:41].[F:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[S:25]([C:28]1[C:36]2[C:31](=[C:32]([O:37][CH2:38][CH2:39][NH2:40])[CH:33]=[CH:34][CH:35]=2)[NH:30][CH:29]=1)(=[O:26])=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 62649Sodium sulfate decahydrateHCID 220193922-[3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine

Product 1

HCID 220193912-[3-(2-Fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine hydrochlorideYield 11%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A dry 25 mL roundbottom flask was equipped with a magnetic stirrer and purged with argon gas. To this was added via syringe a solution of [3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-acetonitrile in 10 mL of anhydrous THF. The flask was cooled to 0° C. and lithium aluminum hydride solution was added (1 mL of 1M solution in THF) dropwise over 2 minutes via syringe. The reaction was allowed to warm to room temperature. After 1 hour, the reaction mixture was combined with 25 mL diethyl ether and quenched with sodium sulfate decahydrate (0.371 g., 1.14 mmol). The resulting suspension was stirred for 2 hours, filtered through a bed of celite and concentrated in vacuo. The resulting residue was purified by flash chromatography (neat CH2Cl2 to 10:1:0.1, CH2Cl2:MeOH:NH4OH over 35 minutes) to give 0.138 g. of the free base 2-[3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine. The solid was dissolved in 1 mL ethanol, to which was added 0.5 mL of 2N ethanolic HCl. The resulting solution was concentrated in vacuo and triturated with 45 mL cold ethyl ether to give 110 mg of 2-[3-(2-Fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-ethylamine hydrochloride as a purple powder (11%). (M−H)−=333.

Workup

  1. customA dry 25 mL roundbottom flask was equipped with a magnetic stirrer
  2. custompurged with argon gas
  3. additionTo this was added via syringe a solution of [3-(2-fluoro-benzenesulfonyl)-1H-indol-7-yloxy]-acetonitrile in 10 mL of anhydrous THF
  4. additionlithium aluminum hydride solution was added (1 mL of 1M solution in THF) dropwise over 2 minutes via syringe
  5. temperatureto warm to room temperature
  6. filtrationfiltered through a bed of celite and
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by flash chromatography (neat CH2Cl2 to 10:1:0.1, CH2Cl2:MeOH:NH4OH over 35 minutes)
  9. customto give 0.138 g
  10. concentrationThe resulting solution was concentrated in vacuo
  11. customtriturated with 45 mL cold ethyl ether

Sources & evidence

ORD record
ord-28ef4f87f29444f4ab29c44206c85e6f
Source dataset
uspto-grants-2006_08
Patent number
US07084169B2

Linked notes

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