HCID 21071873, compound → HCID 21071891, compound

HRID 1372413Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]1([C:13](=O)[CH2:14][CH2:15][C:16]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[NH:18][CH:17]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1>O1CCCC1.[OH-].[Na+]>[N:7]1([CH2:13][CH2:14][CH2:15][C:16]2[C:24]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]=3[NH:18][CH:17]=2)[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 1.9 g (50 mmol) of lithium aluminum hydride in 30 mL of tetrahydrofuran was added dropwise a solution of 11.3 g (43 mmol) of 1-morpholin-4-yl-3-(4,5,6,7-tetrahydro-1H-indol-3-yl)-propan-1-one in 20 mL of tetrahydrofuran. The reaction mixture was stirred at 80° C. for 2.5 hours and then cooled in an ice bath. Ice cubes were slowly added to the reaction mixture until no more gas was generated. A few drops of 2 N sodium hydroxide were added and the reaction mixture was stirred at room temperature for 30 minutes, extracted with ethyl acetate and the extract dried over anhydrous sodium sulfate and concentrated to give 9.2 g (89% yield) of 3-(3-morpholin-4-yl-propyl)-4,5,6,7-tetrahydro-1H-indole as a red oil which was used without further purification.

Workup

temperaturecooled in an ice bath
additionIce cubes were slowly added to the reaction mixture until no more gas
stirringthe reaction mixture was stirred at room temperature for 30 minutes
extractionextracted with ethyl acetate
dry with materialthe extract dried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-83b5126a736147f0bd21f0406e51df30
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157577B2

Reaction notes

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