[2-(3-Cyano-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester → 3-(2-Amino-propyl)-benzonitrile

HRID 1785426Notes

Reaction equation

HRID 1785426 reaction equation
C(OC(=O)[NH:7][CH:8]([CH3:18])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH2:7][CH:8]([CH3:18])[CH2:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=1)[C:16]#[N:17]

Participants

4

Reactant 1

HCID 69068307[2-(3-Cyano-phenyl)-1-methyl-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 575931503-(2-Amino-propyl)-benzonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of [2-(3-Cyano-phenyl) -1-methyl-ethyl]-carbamic acid tert-butyl ester (180 mg, 0.69 mmol) in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was stirred for 15 min at room temperature. Solvents removed under vacuum, and residue was partitioned between dichloromethane and 1 N sodium hydroxide. Organic dried over magnesium sulfate and reduced to an oil under vacuum. M+1=161.

Workup

  1. customSolvents removed under vacuum, and residue
  2. customwas partitioned between dichloromethane and 1 N sodium hydroxide
  3. dry with materialOrganic dried over magnesium sulfate

Sources & evidence

ORD record
ord-8eed1f6741c94565b214f88940a313f8
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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