Trifluoroacetic acid → 4-(Aminomethyl)benzonitrile

HRID 887261Notes

Reaction equation

HRID 887261 reaction equation
C(OC([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[CH:19][CH:18]=1)C(OC(C)(C)C)=O)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:24][CH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:16]#[N:8])=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 3683768Tert-butyl N-[(4-cyanophenyl)methyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamate

Product 1

HCID 826084-(Aminomethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N,N-bis(tert-butoxycarbonyl)-4-cyanobenzylamine (0.75 g, 2.25 mmol, prepared according to the literature described in Synthetic Communications 4419:28 (1998), in CH2Cl2 (15 mL) was treated with trifluoroacetic acid (8 mL). After stirring at room temperature for 3 hours, the mixture was concentrated under reduced pressure and the residue was azeotroped with diethyl ether.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customthe residue was azeotroped with diethyl ether

Sources & evidence

ORD record
ord-25d9167931af4b95b23a56ba7ae42a65
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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