Triethylamine → benzyl N-pyridin-3-ylcarbamate

HRID 2396500Notes

Reaction equation

HRID 2396500 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=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]>ClCCl>[C:16]([NH:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 10387Benzyl chloroformate

Product 1

HCID 4323589benzyl N-pyridin-3-ylcarbamateYield 39.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-aminopyridine (10 g, 0.106 mol) and triethyl amine (16.3 mL, 0.117 mol) in dichloromethane (100 mL) at 0° C., was added benzyl chloroformate (15.2 mL, 0.106 mol) slowly. The reaction mixture was stirred overnight and was washed with water, saturated NaHCO3, dried over MgSO4, and evaporated. The residue was purified on a silica gel column to give the product (9.51 g)

Workup

  1. washwas washed with water, saturated NaHCO3
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-21302e956b554cc7913f7c0fb9fb4cf0
Source dataset
uspto-grants-1996_02
Patent number
US05492916

Reaction notes

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