2-[4-(Aminomethyl)phenyl]benzonitrile → HCID 10457125, compound

HRID 1742115Notes

Reaction equation

HRID 1742115 reaction equation
[CH2:1]([N:8]([CH3:23])[C:9](=[O:22])[C:10](=O)[NH:11][N:12]=[C:13](OCC)[CH2:14][CH2:15][CH2:16][CH3:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH2:39])=[CH:34][CH:33]=1)#[N:25]>C(O)C>[CH2:1]([N:8]([CH3:23])[C:9]([C:10]1[N:39]([CH2:38][C:35]2[CH:34]=[CH:33][C:32]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=3[C:24]#[N:25])=[CH:37][CH:36]=2)[C:13]([CH2:14][CH2:15][CH2:16][CH3:17])=[N:12][N:11]=1)=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrileHCID 86748068HCID 86748068, compound

Product 1

HCID 10457125HCID 10457125, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 319 mg (1 mmole) of ethyl valerate 5-benzyl-5-methylsemioxamazone (from Step C), 312 mg (1.5 mmole) of [(2'-cyanobiphenyl-4-yl)methyl]amine (from Step D), and 3 ml of dry ethanol was stirred under N2 in an oil bath at 50° C. for 2 hours and then at 70° C. for an additional 22 hours. The solution was concentrated in vacuo, and a solution of the residue in 30 ml of ethyl acetate was washed with 2×25 ml of 2 N HCl followed by 25 ml of saturated NaHCO3. The dried (MgSO4) ethyl acetate phase was filtered and concentrated. Column chromatography of the residue on silica gel (gradient elution using 0.25-5% isopropanol in CH2Cl2 gave 353 mg (76%) of the title compound as a hard glass, mp >40° C. (gradual), homogeneous by TLC in 19:1 CH2Cl 2 --MeOH; mass spectrum (FAB) m/e 464 (M+i)+. NMR indicated approximately a 1:1 ratio of amide rotamers.

Workup

  1. waitat 70° C. for an additional 22 hours
  2. concentrationThe solution was concentrated in vacuo
  3. washa solution of the residue in 30 ml of ethyl acetate was washed with 2×25 ml of 2 N HCl
  4. dry with materialThe dried (MgSO4) ethyl acetate phase
  5. filtrationwas filtered
  6. concentrationconcentrated
  7. washColumn chromatography of the residue on silica gel (gradient elution

Sources & evidence

ORD record
ord-fe12f0dbf1ed47629a2df6042496a449
Source dataset
uspto-grants-1994_08
Patent number
US05336778

Reaction notes

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