Triethylamine → HCID 66731516, compound

HRID 1963191Notes

Reaction equation

HRID 1963191 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH:13]([C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][N:10]2[C:19]([O:21][CH3:22])=[O:20])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br-].[Li+].C(N(CC)CC)C>C(#N)C.O.CC(OC)(C)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][CH2:11][N:10]2[C:19]([O:21][CH3:22])=[O:20])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 82050Lithium BromideHCID 68503986HCID 68503986, compound

Product 1

HCID 66731516HCID 66731516, compoundYield 90.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Dimethyl 2-(3,5-dichlorophenyl)piperidine-1,4-dicarboxylate (5.3 g, 15.31 mmol) was dissolved in acetonitrile (51.7 mL). Water (1.033 mL), lithium bromide (10.64 g, 122.47 mmol) and triethylamine (8.53 mL, 61.24 mmol) were added and the resulting mixture was heated under reflux for 2.5 h. It was diluted with water and MTBE. The aqueous layer was extracted with water. The combined aqueous layers were acidified with 3 M HCl, extracted with MTBE, dried over MgSO4, filtered and evaporated to give 2-(3,5-dichlorophenyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (4.60 g, 90%) as a greenish foam. MS m/z 330 (M−H)−

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 2.5 h
  3. extractionThe aqueous layer was extracted with water
  4. extractionextracted with MTBE
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-d380d31756294c1d9df217155303d895
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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