2-Biphenylacetonitrile → 2-([1,1'-Biphenyl]-2-yl)ethanamine

HRID 1666804

Reaction equation

HRID 1666804 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][C:14]#[N:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C(OCC)C>[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[CH2:13][CH2:14][NH2:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 3341012-BiphenylacetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 219212422-([1,1'-Biphenyl]-2-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Combine 2-phenylphenylacetonitrile (4.69 g, 24.26 mmol) and diethyl ether (10 ml) and add dropwise to a cooled (−10°) solution of LiAlH4 (2.76 g, 72.81 mmol) in diethyl ether (100 ml). Warm to ambient temperature. After 2 hours, quench with saturated sodium sulfate (100 mL/mol). Filter to remove the precipitate, dry (Na2SO4) the filtrate, filter, and concentrate to residue. Chromatograph the residue on silica gel eluting with dichloromethane/2N NH3(methanol) (95/5) to give the title compound as a yellow oil. Prepare the HCl salt in diethyl ether: mp 197-199° C. MS (ACPI): m/e 198.1 (M+1). Analysis for C14H16ClN: Calcd: C, 71.94; H, 6.90; N, 5.99. found: C, 72.15; H, 6.84; N, 6.09.

Workup

  1. customquench with saturated sodium sulfate (100 mL/mol)
  2. filtrationFilter
  3. customto remove the precipitate
  4. dry with materialdry (Na2SO4) the filtrate
  5. filtrationfilter
  6. concentrationconcentrate to residue

Sources & evidence

ORD record
ord-5c80fa2c92144ba9abd526d258a4a96d
Source dataset
uspto-grants-2011_10
Patent number
US08044090B2

Linked notes

Loading…