Tert-butyl N-[(4-cyanophenyl)methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate → 4-(Aminomethyl)benzonitrile

HRID 1186908Notes

Reaction equation

HRID 1186908 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1)C(OC(C)(C)C)=O)=O)(C)(C)C>C(O)(C(F)(F)F)=O.ClCCl>[NH2:22][CH2:21][C:20]1[CH:23]=[CH:24][C:17]([C:16]#[N:8])=[CH:18][CH:19]=1

Participants

4

Reactant 1

HCID 3683768Tert-butyl N-[(4-cyanophenyl)methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

Product 1

HCID 826084-(Aminomethyl)benzonitrileYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

4-(Di-tert-butoxycarbonylaminomethyl)benzonitrile (2 g, 6.0 mmoles) (prepared as described in Preparative Example 247, Step A above) was dissolved in TFA (4 mL) and the solution was stirred at 25° C. for 0.25 h. The reaction mixture was diluted with dichloromethane and extracted with 1N sodium hydroxide. The organic layer was dried (MgSO4), filtered and evaporated to dryness. The residue was chromatographed on a silica gel column (15×5 cm) using 3% (10% conc. ammonium hydroxide in methanol)-dichloromethane as the eluant to give 4-(aminomethyl)benzonitrile (108 mg, 68%): FABMS: m/z 133.1 (MH+); HRFABMS: m/z 133.0764 (MH+). Calcd. for C8H9N2: m/z 133.0766; δH (CDCl3) 2.04 (2H, s, —CH2NH2), 3.89 (2H, s, —CH2NH2), 7.40 (2H, d, Ar—H) and 7.59 ppm (2H, d, Ar—H); δC (CDCl3)CH2: 45.7; CH: 127.8, 127.8, 132.4, 132.4; C: 110.6, 118.9, 148.0.

Workup

  1. extractionextracted with 1N sodium hydroxide
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was chromatographed on a silica gel column (15×5 cm)

Sources & evidence

ORD record
ord-12c2a58a6f3c4b9eb21eaa61729e817f
Source dataset
uspto-grants-2014_03
Patent number
US08673924B2

Reaction notes

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