3-(cyclohexylamino)-2-(phenylmethylene)-3H-inden-1-one → HCID 68750424, compound

HRID 59018Notes

Reaction equation

HRID 59018 reaction equation
[CH:1](=[C:8]1[CH:16]([NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH:1](=[C:8]1[CH:16]([NH:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[OH:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4229813-(cyclohexylamino)-2-(phenylmethylene)-3H-inden-1-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 68750424HCID 68750424, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Benzylidene-3-cyclohexylamino-indan-1-one (3, BCI) (317 mg, 1 mmol) was dissolved in dry THF (15 mL) under nitrogen. Solution of LiAlH4 (76 mg, 2 mmol) in dry THF (10 mL) was added dropwise at 0° C. Solution was stirred overnight and quenched with 100 μL of water followed by 100 μL of 15% NaOH followed by 300 μL of water. Precipitate was filtered off and washed with ether (3×30 mL). Combined liquid was evaporated in vacuum, and residue was separated by column chromatography on silica (DCM-MeOH—NH4OH 100:1:0.5).

Workup

  1. customquenched with 100 μL of water
  2. filtrationPrecipitate was filtered off
  3. washwashed with ether (3×30 mL)
  4. customwas evaporated in vacuum, and residue
  5. customwas separated by column chromatography on silica (DCM-MeOH—NH4OH 100:1:0.5)

Sources & evidence

ORD record
ord-bf75a23bf707431a9d54a005a006ddd1
Source dataset
uspto-grants-2016_09
Patent number
US09439877B2

Reaction notes

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