Triethylamine → 1-Benzyloxycarbonyl-4-(3-pyridyl)-1,2,3,4-tetrahydropyridine

HRID 2256041Notes

Reaction equation

HRID 2256041 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:18]1[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=1.C(N(CC)CC)C>CS(C)=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH:12]=[CH:13][CH:14]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 122863-BromopyridineHCID 15637681Benzyl 3,4-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 190291131-Benzyloxycarbonyl-4-(3-pyridyl)-1,2,3,4-tetrahydropyridineYield 6.1%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1-benzyloxycarbonyl-1,2,3,4-tetrahydropyridine (8.69 g) in dimethylsulfoxide (50 mL) was treated with 3-bromopyridine (6.32 g), triethylamine (5.6 mL) and palladium(II) acetate (0.499 g). The reaction mixture was heated to 100° C. for 16 hours, cooled to the room temperature, diluted with water, and extracted with ether. The organic layer was washed with water; the combined organic layers were dried and evaporated to produce the crude product. This material was distilled under reduced pressure and the volatile material distilling at 120° C. (66.7 Pa) was removed. The remaining residue was chromatographed, with hexane:ethyl acetate (1:1) as eluent, to afford the coupled product (0.714 g); NMR (CDCl3): 1.7 (broad s, 2), 2.16 (broad m, 1), 3.5-3.7 (m, 2), 4.9-5.1 (d of m, 2), 5.2 (m, 2), 7.0-7.5 (m, 8), 8.5 (m, 2); MS: m/z=295(M+1).

Workup

  1. temperaturecooled to the room temperature
  2. extractionextracted with ether
  3. washThe organic layer was washed with water
  4. customthe combined organic layers were dried
  5. customevaporated
  6. customto produce the crude product
  7. distillationThis material was distilled under reduced pressure
  8. distillationthe volatile material distilling at 120° C. (66.7 Pa)
  9. customwas removed
  10. customThe remaining residue was chromatographed, with hexane:ethyl acetate (1:1) as eluent

Sources & evidence

ORD record
ord-d8c5f4bba1f847e08161ffe5b8046e0a
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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