Hydrochloric Acid → HCID 66734743, compound

HRID 1963206Notes

Reaction equation

HRID 1963206 reaction equation
Cl.[Cl:2][C:3]1[C:8]([F:9])=[CH:7][C:6]([CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]2)=[CH:5][C:4]=1[F:20].CCN(C(C)C)C(C)C.[C:30](Cl)(=[O:33])[O:31][CH3:32].Cl>ClCCl>[Cl:2][C:3]1[C:4]([F:20])=[CH:5][C:6]([CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][N:11]2[C:30]([O:31][CH3:32])=[O:33])=[CH:7][C:8]=1[F:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731669HCID 66731669, compound

Product 1

HCID 66734743HCID 66734743, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-chloro-3,5-difluorophenyl)piperidine-4-carboxylate hydrochloride (1.82 g, 5.58 mmol) was dissolved in dichloromethane (50 mL). DIPEA (2.430 mL, 13.95 mmol) and methyl carbonochloridate (0.527 mL, 6.70 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-(4-chloro-3,5-difluorophenyl)piperidine-1,4-dicarboxylate (1.83 g, 94%). MS m/z 348 (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-aec309f9d52541d6a708e32cb2ce133f
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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