{2-[3-(Benzhydrylidene-amino)-phenyl]-1-methyl-ethyl}-carbamic acid tert-butyl ester → 3-(2-Aminopropyl)aniline

HRID 1785428Notes

Reaction equation

HRID 1785428 reaction equation
C(OC(=O)[NH:7][CH:8]([CH3:30])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]=C(C2C=CC=CC=2)C2C=CC=CC=2)[CH:11]=1)(C)(C)C>ClCCl.FC(F)(F)C(O)=O>[NH2:7][CH:8]([CH3:30])[CH2:9][C:10]1[CH:11]=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 1

HCID 86600374{2-[3-(Benzhydrylidene-amino)-phenyl]-1-methyl-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 204423703-(2-Aminopropyl)aniline

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution {2-[3(Benzhydrylidene-amino)-phenyl]-1-methyl-ethyl}-carbamic acid tert-butyl ester (200 mg, 0.48 mmol) in dichloromethane (5 mL) and trifluoroacetic acid (5 mL) was stirred for 45 min at room temperature. Solvents removed under vacuum and residue suspended in 5 N hydrochloric acid at 60° C. for 20 min. Biphasic system washed with ether and organics discarded. The pH of the aqueous layer was then adjusted to 14 with 10 N sodium hydroxide. Aqueous was then washed three times with dichloromethane (10 mL). Combined organics dried over magnesium sulfate, and product isolated as an amber film after removal of solvent under vacuum. M+1=151.

Workup

  1. customSolvents removed under vacuum and residue
  2. washBiphasic system washed with ether
  3. washAqueous was then washed three times with dichloromethane (10 mL)
  4. dry with materialCombined organics dried over magnesium sulfate, and product
  5. customisolated as an amber film
  6. customafter removal of solvent under vacuum

Sources & evidence

ORD record
ord-8ecacdfd807041be80650c8a448f0c32
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

Loading…