Triethylamine → HCID 66731984, compound

HRID 1963233Notes

Reaction equation

HRID 1963233 reaction equation
[CH:1]1([CH:7]2[CH2:12][CH:11]([C:13]([O:15]C)=[O:14])[CH2:10][CH2:9][N:8]2[C:17]([O:19][CH3:20])=[O:18])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Br-].[Li+].C(N(CC)CC)C.CC(OC)(C)C>C(#N)C.O>[CH:1]1([CH:7]2[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10][CH2:9][N:8]2[C:17]([O:19][CH3:20])=[O:18])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 82050Lithium BromideHCID 66732522HCID 66732522, compound

Product 1

HCID 66731984HCID 66731984, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

Dimethyl 2-cyclohexylpiperidine-1,4-dicarboxylate (4.90 g, crude) was dissolved in acetonitrile (30 mL) and water (0.600 mL). lithium bromide (9.28 g, 106.80 mmol) and triethylamine (7.40 mL, 53.40 mmol) were added and the mixture was heated under reflux for 2 h. Water (60 mL) and MTBE were added. The organic phase was extracted with water (×2). MTBE was added to the pooled aqueous layer and the solution was acidified to pH 1 with 2 M HCl and then extracted with MTBE (×2). The combined organic layer was dried over Na2SO4 and evaporated to give 2-cyclohexyl-1-(methoxycarbonyl)piperidine-4-carboxylic acid (3.28 g, 91% (over 2 steps)) as a slightly yellow semisolid. MS m/z 270 (M+H)+

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractionThe organic phase was extracted with water (×2)
  4. additionMTBE was added to the pooled aqueous layer
  5. extractionextracted with MTBE (×2)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-9eda72da9bca4f99987632f4191df53b
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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