Triethylamine → Benzyl 4-aminobenzylcarbamate

HRID 1599714Notes

Reaction equation

HRID 1599714 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[CH:4][CH:3]=1.[CH2:10]([O:17][C:18](Cl)=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:18](=[O:19])[O:17][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 4278144-Aminobenzylamine

Product 1

HCID 2757381Benzyl 4-aminobenzylcarbamateYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminobenzenemethanamine (1.5 g, 12.3 mmol) in 20 mL CH2Cl2 was added benzylchloroformate (1.57 mL, 11 mmol), followed by triethylamine (Et3N) (1.5 mL, 11 mmol) at room temperature. White percipitates was observed immediately. The reaction was stirred at room temperature for 10 minutes and removed Et3N salt by filtration. The reaction mixture was concentrated in vacuo and partitioned between EtOAc and H2O. The EtOAc layer was washed with a sat. solution of KHSO4, a sat. solution of NaHCO3, concentrated in vacuo and subjected to a silica-gel column using CHCl3 /CH3 OH=25/1 ratio as an eluting solvent to give title compound (43% yield).

Workup

  1. customremoved Et3N salt
  2. filtrationby filtration
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompartitioned between EtOAc and H2O
  5. washThe EtOAc layer was washed with a sat. solution of KHSO4
  6. concentrationa sat. solution of NaHCO3, concentrated in vacuo

Sources & evidence

ORD record
ord-70c92724924f40e9aff39668dc762cfb
Source dataset
uspto-grants-1998_04
Patent number
US05741792

Reaction notes

Loading…