Aluminium lithium hydride → HCID 22396944, compound

HRID 1370356Notes

Reaction equation

HRID 1370356 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([N:15]1[CH2:28][CH2:27][C:26]2[C:25]3[CH:24]=[C:23]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:22]=[CH:21][C:20]=3[NH:19][C:18]=2[CH2:17][CH2:16]1)(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CCOC(C)=O.CCCCCCC>O1CCCC1>[CH2:7]([N:15]1[CH2:28][CH2:27][C:26]2[C:25]3[CH:24]=[C:23]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:22]=[CH:21][C:20]=3[NH:19][C:18]=2[CH2:17][CH2:16]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 21899848Ethylacetate heptaneHCID 22396758HCID 22396758, compound

Product 1

HCID 22396944HCID 22396944, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride (0.17 g, 4.45 mmol) in tetrahydrofuran (3.0 mL) and a solution of 3-benzoyl-9-phenyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (0.17 g, 0.46 mmol) in tetrahydrofuran (5.0 mL) at 0° C. were reacted in a manner similar to Example 1 to give an oil. Column chromatography (silica gel, 10-50% EtOAc/heptane) afforded 0.113 g (71%) of the title compound as an oil. 1H NMR (300 MHz, CDCl3) δ 8.05, 7.66-7.57, 7.49, 7.45-7.30, 7.13-7.04, 3.98, 3.18-2.97; MS (EI) m/z 366 (M+); HRMS (FAB) calcd for C25H24N2+H: 353.2018, found: 353.2021.

Workup

  1. customto give an oil

Sources & evidence

ORD record
ord-6fe7c701da954245b7892756e7771122
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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