Triethylamine → 1-[(2-Methoxy-3-piridyl)methyl]-4-(2,2-dibromovinyl)piperidine

HRID 1837689Notes

Reaction equation

HRID 1837689 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH2:16]C=O)[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1.C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:45]([Br:49])(Br)(Br)[Br:46]>ClC(Cl)C.ClCCl>[CH3:1][O:2][C:3]1[C:8]([CH2:9][N:10]2[CH2:15][CH2:14][CH:13]([CH:16]=[C:45]([Br:49])[Br:46])[CH2:12][CH2:11]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 226783021-[(2-Methoxy-3-pyridyl)methyl]-4-piperidineacetaldehyde

Product 1

HCID 226784931-[(2-Methoxy-3-piridyl)methyl]-4-(2,2-dibromovinyl)piperidineYield 61.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

3.0 g of 1-[(2-methoxy-3-piridyl)methyl]-4-piperidine acetaldehyde, 5.4 ml of triethylamine, 20.1 g of triphenylphosphine and 12.9 g of carbon tetrabromide were dissolved in 77 ml of dichloroethane at 0° C., and the mixture was stirred for one hour. Dichloromethane was added to the reaction solution, the mixture was washed with an aqueous saturated sodium bicarbonate, and then it was dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by NH form silica gel column chromatography (hexane:ethyl acetate=20:1), to give 2.9 g of the title compound as a yellow oil.

Workup

  1. washthe mixture was washed with an aqueous saturated sodium bicarbonate
  2. dry with materialit was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe crude product was purified by NH
  5. customform silica gel column chromatography (hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-cf7647aa98814464817033709908698a
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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