Triethylamine → N-(phenoxycarbonylamino)-1,2,3,6-tetrahydropyridine

HRID 4359Notes

Reaction equation

HRID 4359 reaction equation
Cl.[NH2:2][N:3]1[CH2:8][CH:7]=[CH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:18]>C(Cl)Cl>[O:19]([C:17]([NH:2][N:3]1[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8]1)=[O:18])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 193760471,2,3,6-Tetrahydropyridin-1-amine hydrochloride

Product 1

HCID 20152376N-(phenoxycarbonylamino)-1,2,3,6-tetrahydropyridineYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of N-amino-1,2,3,6-tetrahydropyridine hydrochloride (1.346 g) and triethylami-ne (2.024 g) in methylene chloride (60 ml) was added a solution of phenyl chloroformate (1.566 g) in methylene chloride (40 ml) and the mixture was stirred for 4 hours at 5° C. Evaporation of the solvent gave a residue, which was extracted with ethyl acetate (150 ml). The extract was washed with water and dried over magnesium sulfate. The solvent was evaporated in vacuo to give N-(phenoxy- carbonylamino)-1,2,3,6-tetrahydropyridine (2.01 g), which was recrystallized from diisopropyl ether to give the desired compound (0.732 g) as colorless needles. mp: 124°-125.5° C.

Workup

  1. customEvaporation of the solvent
  2. customgave a residue, which
  3. extractionwas extracted with ethyl acetate (150 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c74194e3c47f4eb68794e86e6dfaa233
Source dataset
uspto-grants-1988_02
Patent number
US04725608

Reaction notes

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