Triethylamine → Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

HRID 2355523Notes

Reaction equation

HRID 2355523 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16]>C(Cl)Cl.CCOCC>[N:1]1([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:2][CH2:3][CH:4]=[CH:5][CH2:6]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 127501,2,3,6-Tetrahydropyridine

Product 1

HCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 1,2,3,6-tetrahydropyridine (5.0 g, 60.15 mmol) and triethylamine (16.77 mL, 2 equiv) in CH2Cl2 (50 mL) was cooled to 0° C. (ice/water bath), Benzyl chloroformate (9.7 mL, 1.1 equiv) was added slowly. After 30 min, the reaction mixture was allowed to warm slowly to rt and stirred for 4 h. LC-MS showed the reaction was complete. The mixture was diluted with ether (300 mL), washed with 5% aq HCl (2×50 mL), satd aq NaHCO3 (40 mL) and brine (40 mL), and dried over Na2SO4. After concentration, benzyl 5,6-dihydropyridine-1(2H)-carboxylate (9.93 g, 78% yield) was left. LC-MS (3 min) tR=1.74 min., m/z 218 (M+1).

Workup

  1. additionwas added slowly
  2. washwashed with 5% aq HCl (2×50 mL)
  3. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-d978655c71a0439d9e21d5eff3cc4152
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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