tert - butyl (3 - cyanobenzyl)carbaMate → Benzonitrile, 3-(aminomethyl)-

HRID 2071049Notes

Reaction equation

HRID 2071049 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][NH:7]C(=O)OC(C)(C)C)#[N:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][CH2:6][C:5]1[CH:4]=[C:3]([CH:17]=[CH:16][CH:15]=1)[C:1]#[N:2]

Participants

4

Reactant 1

HCID 62313508tert - butyl (3 - cyanobenzyl)carbaMate

Product 1

HCID 457594Benzonitrile, 3-(aminomethyl)-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To tert-butyl 3-cyanobenzylcarbamate in CH2Cl2 (10 ml), TFA (3 ml) was added. After 1 h, volatiles were removed on a rotavap under reduced pressure. Crude residue 3-(aminomethyl)benzonitrile was dissolved in water, basified with 2N NaOH and extracted with CHCl3 (100 ml) and used without further purification.

Workup

  1. customvolatiles were removed on a rotavap under reduced pressure
  2. dissolutionCrude residue 3-(aminomethyl)benzonitrile was dissolved in water
  3. extractionextracted with CHCl3 (100 ml)
  4. customused without further purification

Sources & evidence

ORD record
ord-649b53764989433388bac4e75482b71c
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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