Triethylamine → N-[(tert-butylcarbamoyl)amino]-1,2,3,6-tetrahydropyridine

HRID 2309181Notes

Reaction equation

HRID 2309181 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:9][N:10]1[CH2:15][CH:14]=[CH:13][CH2:12][CH2:11]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([NH:5][C:6]([NH:9][N:10]1[CH2:11][CH:12]=[CH:13][CH2:14][CH2:15]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62412tert-Butyl isocyanateHCID 193760471,2,3,6-Tetrahydropyridin-1-amine hydrochloride

Product 1

HCID 20185946N-[(tert-butylcarbamoyl)amino]-1,2,3,6-tetrahydropyridineYield 25.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of tert-butyl isocyanate (0.991 g) in methylene chloride (8 ml) was added dropwise to a mixture of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylamine (1.012 g) in methylene chloride (40 ml) under ice bath cooling. The mixture was stirred for an hour at about 5° C. The reaction mixture was evaporated to dryness, and then the residue was dissolved in ethyl acetate (50 ml). The solution was washed with water (40 ml), dried over magnesium sulfate and evaporated to dryness. The crude residue was washed with ether and dried to give N-[(tert-butylcarbamoyl)amino]-1,2,3,6-tetrahydropyridine (0.50 g).

Workup

  1. temperaturecooling
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in ethyl acetate (50 ml)
  4. washThe solution was washed with water (40 ml)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. washThe crude residue was washed with ether
  8. customdried

Sources & evidence

ORD record
ord-b1cb866376ef4bc0b0bf3d81c13661c8
Source dataset
uspto-grants-1987_09
Patent number
US04694004

Reaction notes

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