1-Chloroethyl chloroformate → 2,3-Dihydrospiro(benzofuran-2,3'-piperidine)

HRID 1781365노트

반응식

HRID 1781365 반응식
C([N:8]1[CH2:13][CH2:12][CH2:11][C:10]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9]1)C1C=CC=CC=1.ClC(OC(Cl)=O)C>ClC(Cl)C>[NH:8]1[CH2:13][CH2:12][CH2:11][C:10]2([CH2:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14]2)[CH2:9]1

참가 물질

4

반응물 2

HCID 5213051-Chloroethyl chloroformateHCID 19045403HCID 19045403, 화합물

생성물 1

HCID 190452922,3-Dihydrospiro(benzofuran-2,3'-piperidine)수율 94.2%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

A solution of 13 g (46 mmole) of 1'-benzyl-2,3-dihydrospiro(benzofuran-2,3'-piperidine) in 100 mL dichloroethane was treated with 7.31 g (5.2 mL, 51 mmoles) of 1-chloroethylchloroformate at room temperature for 1/2 hour. The reaction mixture was concentrated and the residue dissolved in CH3OH and heated to reflux for 1/2 hour. The methanol was evaporated at reduced pressure, and the residue partitioned between ethyl acetate and 1 N HCl. The ethyl acetate layer was discarded and the aqueous phase was basified to pH 9 and reextracted with ethyl acetate. The ethyl acetate solution was dried over magnesium sulfate, filtered and concentrated in vacuo to give 8.2 g product.

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in CH3OH
  3. temperatureheated
  4. temperatureto reflux for 1/2 hour
  5. customThe methanol was evaporated at reduced pressure
  6. customthe residue partitioned between ethyl acetate and 1 N HCl
  7. dry with materialThe ethyl acetate solution was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-497ce0dac18148448d14e82b382fc215
출처 데이터셋
uspto-grants-1997_05
특허 번호
US05633247

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