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

HRID 459728

Reaction equation

HRID 459728 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-f593e037c460410a877e4f4ad2e2c590
Source dataset
uspto-grants-2007_03
Patent number
US07196078B2

Linked notes

Loading…