4-Acetylbiphenyl → HCID 58503934, compound

HRID 2407798Notes

Reaction equation

HRID 2407798 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.[C:16]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:20][C:19]([C:22](=O)[CH3:23])=[CH:18][CH:17]=1.[C:31]([Al](CC)CC)#[N:32]>ClCCl.C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[C:16]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:21]=[CH:20][C:19]([C:22]([N:1]2[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3][CH2:2]2)([C:31]#[N:32])[CH3:23])=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 71134-AcetylbiphenylHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 16683962(cyano-C)diethylaluminium

Product 1

HCID 58503934HCID 58503934, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To tert-butyl piperidin-4-ylmethylcarbamate (0.527 g) and 1-(biphenyl-4-yl)ethanone (0.483 g) in dichloromethane (6.2 mL) was added titanium (IV) isopropoxide (0.720 mL). The reaction mixture was stirred at room temperature for 24 hours. A 1.0 mol/L solution of cyanodiethylaluminum (2.46 mL) in toluene was then added dropwise and the reaction mixture was stirred at ambient temperature for another 24 hours. It was then quenched with saturated sodium bicarbonate and diluted with dichloromethane. The biphasic mixture was filtered, and the layers of the filtrate were separated. The aqueous layer was extracted with dichloromethane, and the combined organics were dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate:hexanes=85:15) to obtain the title compound (0.565 g) having the following physical data.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for another 24 hours
  2. customIt was then quenched with saturated sodium bicarbonate
  3. additiondiluted with dichloromethane
  4. filtrationThe biphasic mixture was filtered
  5. customthe layers of the filtrate were separated
  6. extractionThe aqueous layer was extracted with dichloromethane
  7. dry with materialthe combined organics were dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel (ethyl acetate:hexanes=85:15)

Sources & evidence

ORD record
ord-d5d53c66fe7e454c9b33dfa8f7cc33f3
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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