Triethylamine → HCID 71138476, compound

HRID 1852912Notes

Reaction equation

HRID 1852912 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.S(Cl)(Cl)=O.Cl.[CH3:22][NH:23][CH3:24].C(N(CC)CC)C>O1CCOCC1.O.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([N:23]([CH3:24])[CH3:22])=[O:16])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10473Dimethylamine, hydrochlorideHCID 24386Thionyl ChlorideHCID 695708831-(3-Bromophenyl)piperidine-4-carboxylic acid

Product 1

HCID 71138476HCID 71138476, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1-(3-bromophenyl)piperidine-4-carboxylic acid (2 g, 7.0 mmol) in dioxane (70 mL), was added thionyl chloride (2.6 mL, 35 mmol) at 0° C. The mixture was kept at rt for 1 h and evaporated. The residue was co-evaporated with dichloromethane and dissolved in dichloromethane (5 mL). To this mixture, were added the mixture of dimethylamine HCl salt (1.7 g, 21 mmol), triethylamine (4.9 mL, 35 mmol) and dichloromethane (20 mL) at 0° C. The mixture was stirred at rt for 1 h and diluted with water and separated. The organic phase was dried and evaporated. The residue was purified with silica gel column chromatography (hexane/ethyl acetate 10:0 to 1:9) to give the titled compound (2.2 g, 100%).

Workup

  1. customevaporated
  2. dissolutiondissolved in dichloromethane (5 mL)
  3. additionTo this mixture, were added
  4. customseparated
  5. customThe organic phase was dried
  6. customevaporated
  7. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate 10:0 to 1:9)

Sources & evidence

ORD record
ord-bea6faba3dac4ee0a95bcb2cf4a19745
Source dataset
uspto-grants-2015_02
Patent number
US08962619B2

Reaction notes

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