Hydrochloric Acid → HCID 66734680, compound

HRID 1963225Notes

Reaction equation

HRID 1963225 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:13]2[CH2:18][CH:17]([C:19]([OH:21])=[O:20])[CH2:16][CH2:15][NH:14]2)[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:11])[F:10].[CH3:22]CN(C(C)C)C(C)C.[C:31](Cl)(=[O:34])[O:32][CH3:33].Cl>ClCCl>[F:2][C:3]1[CH:4]=[C:5]([CH:13]2[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15][N:14]2[C:31]([O:32][CH3:33])=[O:34])[CH:6]=[CH:7][C:8]=1[C:9]([F:12])([F:10])[F:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731710HCID 66731710, compound

Product 1

HCID 66734680HCID 66734680, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Fluoro-4-(trifluoromethyl)phenyl)piperidine-4-carboxylate hydrochloride (3.12 g, 10.22 mmol) was dissolved in dichloromethane (50 mL), then DIPEA (4.45 mL, 25.55 mmol) and methyl carbonochloridate (0.966 mL, 12.26 mmol) were added and the mixture was stirred at room temperature for 3 h. 0.1 M HCl was added and the aqueous layer was extracted with DCM. The combined organic layers were filtered through a phase separator and evaporated to yield dimethyl 2-(3-fluoro-4-(trifluoromethyl)phenyl)piperidine-1,4-dicarboxylate (3.2 g, 86%). MS m/z 364 (M+H)+

Workup

  1. extractionthe aqueous layer was extracted with DCM
  2. filtrationThe combined organic layers were filtered through a phase separator
  3. customevaporated

Sources & evidence

ORD record
ord-a6482fe67648482eb77c5923103918ef
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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