Trifluoroacetic acid → 4-(Aminomethyl)benzonitrile

HRID 585992Notes

Reaction equation

HRID 585992 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 mixuture was concentrated under reduced pressure and the residue was azeotroped with diethyl ether.

Workup

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

Sources & evidence

ORD record
ord-dd60b80001d84cedb391f105cd33e5a6
Source dataset
uspto-grants-2005_08
Patent number
US06933311B2

Reaction notes

Loading…