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

HRID 1963260
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HRID 1963260 반응식
[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
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참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매
2회

실험 절차

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)+

후처리

  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

출처 및 근거

ORD 기록
ord-e81b0c7efe2a425cbc46cbe412d00f67
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415378B2

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