2-[4-(Aminomethyl)phenyl]benzonitrile → HCID 178446847, compound

HRID 2082053Notes

Reaction equation

HRID 2082053 reaction equation
[CH3:1][S:2][C:3](=[NH:14])[NH:4][N:5]=[C:6](OCC)[CH2:7][CH2:8][CH2:9][CH3:10].[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][NH2:30])=[CH:25][CH:24]=1)#[N:16]>CCO>[CH3:1][S:2][C:3](=[NH:14])[NH:4][N:5]=[C:6]([NH:30][CH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:15]#[N:16])=[CH:28][CH:27]=1)[CH2:7][CH2:8][CH2:9][CH3:10]

Participants

4

Reactant 2

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrileHCID 176547448HCID 176547448, compound

Product 1

HCID 178446847HCID 178446847, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5.50 g (25.3 mmol) of ethyl valerate S-methylisothiosemicarbazone (from Step B), 6.55 g (31.5 mmol) of [(2'-cyanobiphenyl-4-yl)methyl]amine (EP 0412594 published Feb. 13, 1991, Merck Case No. 17959IA), and 57 ml of dry EtOH was stirred under N2 at room temperature for 6 days and then concentrated in vacuo at ≤30° C. The residue was chromatographed on a column of silica gel (38×8.8 cm) packed in CH2Cl2. Gradient elution with 0.5-2% MeOH in CH2Cl2 and concentration of combined product fractions gave 6.86 g (71%) of the title compound as a yellow gum; satisfactory purity by TLC in 19:1 CH2Cl2 -MeOH. NMR indicated a mixture of syn and anti isomers.

Workup

  1. concentrationconcentrated in vacuo at ≤30° C
  2. customThe residue was chromatographed on a column of silica gel (38×8.8 cm)
  3. washGradient elution with 0.5-2% MeOH in CH2Cl2 and concentration of combined product fractions

Sources & evidence

ORD record
ord-17a1ae5c5ac04c0082790d6fc4d152f7
Source dataset
uspto-grants-1993_02
Patent number
US05187179

Reaction notes

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