Trifluoroacetic acid → 4-(Aminomethyl)benzonitrile

HRID 2056879Notes

Reaction equation

HRID 2056879 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-84ef163afe8144379af941775134da50
Source dataset
uspto-grants-2008_02
Patent number
US07335678B2

Reaction notes

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