4-Aminopyridine → Dodecyl carbamate

HRID 1025909Notes

Reaction equation

HRID 1025909 reaction equation
[NH2:1]C1C=CN=CC=1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:17]>C(Cl)Cl>[C:16](=[O:17])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[NH2:1]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 90513Dodecyl chloroformate

Product 1

HCID 233116Dodecyl carbamateYield 120.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-aminopyridine (3.00 g, 31.9 mmol) in CH2Cl2 (50 mL) at 0° C. was added triethylamine (5.60 mL, 40.0 mmol) and dodecyl chloroformate (8.70 g, 35.0 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt over 3 h before being poured into saturated aqueous NaHCO3. The product was extracted with CH2Cl2, washed with brine, dried (MgSO4) and concentrated. The crude product was recrystallized from EtOAc/hexanes to give 8.80 g (90% yield) of pure dodecyl carbamate.

Workup

  1. customThe ice bath was removed
  2. additionbefore being poured into saturated aqueous NaHCO3
  3. extractionThe product was extracted with CH2Cl2
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customThe crude product was recrystallized from EtOAc/hexanes

Sources & evidence

ORD record
ord-859e2e30968645fc9d791f2f7c034b95
Source dataset
uspto-grants-2014_05
Patent number
US08729107B2

Reaction notes

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