Hydrochloric Acid → Dimethyl 2-(4-fluorophenethyl)piperidine-1,4-dicarboxylate

HRID 1963260Notes

Reaction equation

HRID 1963260 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][NH:9]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31].Cl>ClCCl>[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][N:9]2[C:29]([O:30][CH3:31])=[O:32])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731797Methyl 2-(4-fluorophenethyl)piperidine-4-carboxylate

Product 1

HCID 86646603Dimethyl 2-(4-fluorophenethyl)piperidine-1,4-dicarboxylateYield 67.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(4-fluorophenethyl)piperidine-4-carboxylate (3.89 g, 14.65 mmol) was dissolved in dichloromethane (150 mL). DIPEA (3.06 mL, 17.58 mmol) was added, followed by methyl carbonochloridate (1.615 mL, 20.51 mmol). The mixture was stirred at room temperature for 2 h. 0.1 HCl and DCM were added. The phases were separated and the aqueous phase was extracted with DCM. The combined organic layers were washed with satd NaHCO3, filtered through a phase separator and evaporated. Dimethyl 2-(4-fluorophenethyl)piperidine-1,4-dicarboxylate (3.19 g, 67%) was isolated. MS m/z 324 (M+H)+

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with DCM
  3. washThe combined organic layers were washed with satd NaHCO3
  4. filtrationfiltered through a phase separator
  5. customevaporated

Sources & evidence

ORD record
ord-e81b0c7efe2a425cbc46cbe412d00f67
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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