4-Aminopyridine → Benzyl carbamate

HRID 1025910Notes

Reaction equation

HRID 1025910 reaction equation
[NH2:1]C1C=CN=CC=1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(Cl)Cl>[C:16](=[O:17])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:1]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 12136Benzyl carbamateYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminopyridine (2.00 g, 21.2 mmol) in CH2Cl2 (30 mL) at 0° C. was added triethylamine (3.50 mL, 25.0 mmol) and benzyl chloroformate (3.10 mL, 22.0 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt overnight before being poured into saturated aqueous NaHCO3. The product was extracted with CH2Cl2, dried (Na2SO4) and concentrated. The crude product was recrystallized from EtOAc to give 2.90 g (60% yield) of pure benzyl carbamate.

Workup

  1. customThe ice bath was removed
  2. additionbefore being poured into saturated aqueous NaHCO3
  3. extractionThe product was extracted with CH2Cl2
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe crude product was recrystallized from EtOAc

Sources & evidence

ORD record
ord-5f8f54803a364712bc0633c2adf96961
Source dataset
uspto-grants-2014_05
Patent number
US08729107B2

Reaction notes

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