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

HRID 2256040Notes

Reaction equation

HRID 2256040 reaction equation
[NH:1]1[CH2:6][CH:5]=[CH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:14]([O:21][C:22](Cl)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[CH2:14]([O:21][C:22]([N:1]1[CH2:2][CH:3]=[CH:4][CH2:5][CH2:6]1)=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

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

Product 1

HCID 11458613Benzyl 5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1,2,3,6-tetrahydropyridine (5.0 g) in dichloromethane (200 mL) was cooled to 0° C. and treated with triethylamine (10.1 mL) followed by benzylchloroformate (10.3 mL). The reaction mixture was stirred for 1 hour at 0° C., diluted with dichloromethane, washed (dilute hydrochloric acid, sodium bicarbonate solution), dried and evaporated. The crude product was distilled to give the N-protected derivative (11.01 g); bp 160°-165° C. (26.7 Pa); NMR (CDCl3): 2.15 (broad, 2), 3.5 (t,2, J=6), 3.96 (m, 2), 5.15 (s, 2), 5.8 (2 broad peaks, 2), 7.4(m, 5); MS: m/z=218(M+1).

Workup

  1. washwashed (dilute hydrochloric acid, sodium bicarbonate solution)
  2. customdried
  3. customevaporated
  4. distillationThe crude product was distilled
  5. customto give the N-protected derivative (11.01 g)

Sources & evidence

ORD record
ord-30f4b3e5d4db46899e0a7a3d7e40769f
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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