Hydrochloric Acid → HCID 59536568, compound

HRID 1963249Notes

Reaction equation

HRID 1963249 reaction equation
[F:1][CH:2]([F:17])[CH:3]1[CH2:8][CH:7]([C:9]([O:11]C)=[O:10])[CH2:6][CH2:5][N:4]1[C:13]([O:15][CH3:16])=[O:14].[OH-].[Li+].Cl.C(Cl)Cl>C1COCC1.O>[F:17][CH:2]([F:1])[CH:3]1[CH2:8][CH:7]([C:9]([OH:11])=[O:10])[CH2:6][CH2:5][N:4]1[C:13]([O:15][CH3:16])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 59536558HCID 59536558, compound

Product 1

HCID 59536568HCID 59536568, compoundYield 99.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Dimethyl 2-(difluoromethyl)piperidine-1,4-dicarboxylate (2.35 g, 9.35 mmol) was dissolved in THF (35 mL) and 1 M lithium hydroxide (12.16 mL, 12.16 mmol) in water was added. The mixture was stirred at room temperature for 3 h, then 1 M HCl and DCM were added and the phases were separated. The aqueous phase was extracted with DCM and the combined organic layers were dried by filtration through a phase separator and evaporated. 2-(Difluoromethyl)-1-(methoxycarbonyl)piperidine-4-carboxylic acid (2.2 g, 99%) was isolated. MS m/z 275 (M−H)−

Workup

  1. customthe phases were separated
  2. extractionThe aqueous phase was extracted with DCM
  3. customthe combined organic layers were dried by filtration through a phase separator
  4. customevaporated

Sources & evidence

ORD record
ord-c4666cb4a12c4dcc96f0f39cfcd801bc
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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