Triethylamine → 1-(3-Chloro-4-fluorobenzoyl)-4-fluoropiperidine-4-carbaldehyde

HRID 1279271Notes

Reaction equation

HRID 1279271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[C:5]([N:7]1[CH2:12][CH2:11][C:10]([F:15])([CH2:13][OH:14])[CH2:9][CH2:8]1)=[O:6].C(N(CC)CC)C>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[F:19])[C:5]([N:7]1[CH2:12][CH2:11][C:10]([F:15])([CH:13]=[O:14])[CH2:9][CH2:8]1)=[O:6]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10755891(3-Chloro-4-fluorophenyl)[4-fluoro-4-(hydroxymethyl)-1-piperidinyl]methanone

Product 1

HCID 154349491-(3-Chloro-4-fluorobenzoyl)-4-fluoropiperidine-4-carbaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.48 g of pyridine-SO3 complex (15.5 mmol) are added in a single portion to a solution of 1.5 g of 1-(3-Chloro-4-fluorobenzoyl)-4-fluoro-4-piperidine-methanol (5.18 mmol), 2.16 ml of triethylamine (15.5 mmol) and 15 ml of anhydrous DMSO. After stirring for 3 hours at room temperature, the yellow solution obtained is poured into an ice-water mixture and extracted twice with ethyl acetate. The organic phases are washed with aqueous 5% citric acid solution and then with salt water, dried over MgSO4 and filtered and the solvent is removed under vacuum. 1.49 g (quantitative yield) of a yellow oil are obtained, this product being used without further purification in the following step.

Workup

  1. customthe yellow solution obtained
  2. extractionextracted twice with ethyl acetate
  3. washThe organic phases are washed with aqueous 5% citric acid solution
  4. dry with materialwith salt water, dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed under vacuum

Sources & evidence

ORD record
ord-1e6e99c8a19c49c2be4e7e06b0ac8140
Source dataset
uspto-grants-2002_09
Patent number
US06448268B1

Reaction notes

Loading…