Triethylamine → Benzyl 4-aminobenzylcarbamate

HRID 1080850Notes

Reaction equation

HRID 1080850 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 /CH3OH=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-018e39b62ef0400799923e40ee9b38f4
Source dataset
uspto-grants-1996_12
Patent number
US05583146

Reaction notes

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