Triethylamine → HCID 66731707, compound

HRID 1963179Notes

Reaction equation

HRID 1963179 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F: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.CC(OC)(C)C>C(#N)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([F: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 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 86646599HCID 86646599, compound

Product 1

HCID 66731707HCID 66731707, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-(2-chloro-4-fluorophenyl)piperidine-1,4-dicarboxylate (2.5 g, 7.58 mmol) was dissolved in acetonitrile (50 mL) and water (1 mL), then lithium bromide (5.27 g, 60.65 mmol) was added. Triethylamine (4.20 mL, 30.33 mmol) was added and the resulting suspension was heated under reflux for 7 h. MTBE (170 mL) and water (90 mL) were added, the phases separated and the organic layer was extracted with water. The combined aqueous layers were acidified with 3.8 M HCl and extracted with EtOAc. The combined organic layers were dried with Na2SO4 and evaporated. 2-(2-Chloro-4-fluorophenyl)-1-(methoxycarbonyl)-piperidine-4-carboxylic acid (2.130 g, 89%) was isolated as a brown solid. MS m/z 316 (M+H)+

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 7 h
  3. customthe phases separated
  4. extractionthe organic layer was extracted with water
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-4f540b3577164809bf48cf0362480990
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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