Triethylamine → HCID 66731635, compound

HRID 1963187Notes

Reaction equation

HRID 1963187 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH:13]([C:15]([O:17]C)=[O:16])[CH2:12][CH2:11][N:10]1[C:19]([O:21][CH3:22])=[O:20].[Br-].[Li+].C(N(CC)CC)C>C(#N)C.O.CC(OC)(C)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH:13]([C:15]([OH:17])=[O:16])[CH2:12][CH2:11][N:10]1[C:19]([O:21][CH3:22])=[O:20]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 82050Lithium BromideHCID 66734975HCID 66734975, compound

Product 1

HCID 66731635HCID 66731635, compoundYield 91.5%

Reagents, catalysts & solvents 3

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

Procedure

Dimethyl 2-(2,4-dichlorophenyl)piperidine-1,4-dicarboxylate (2.78 g, 8.03 mmol) was dissolved in acetonitrile (27.1 mL) and water (0.542 mL). Lithium bromide (5.58 g, 64.24 mmol) and triethylamine (4.48 mL, 32.12 mmol) were added and the resulting mixture heated under reflux for 4 h, diluted with Water and MTBE and the organic layer 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-(2,4-dichlorophenyl)-1-(methoxy-carbonyl)piperidine-4-carboxylic acid (2.440 g, 91%) as a foam. MS m/z 332 (M+H)+

Workup

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

Sources & evidence

ORD record
ord-96ec863da0074661b072efff3379791c
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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