Formaldehyde → 1-Methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

HRID 2072804노트

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HRID 2072804 반응식
[F:1][C:2]1[C:14]([F:15])=[C:13]([F:16])[C:12]([F:17])=[C:11]([F:18])[C:3]=1[O:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH2:19]=O.[BH4-].[Na+]>CO.C(OCC)(=O)C>[CH3:19][N:8]1[CH2:9][CH2:10][CH:5]([O:4][C:3]2[C:11]([F:18])=[C:12]([F:17])[C:13]([F:16])=[C:14]([F:15])[C:2]=2[F:1])[CH2:6][CH2:7]1

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 148370404-(2,3,4,5,6-Pentafluorophenoxy)piperidine

생성물 1

HCID 148370411-Methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirring solution of 5.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)piperidine in 50 ml of methanol was added 15 ml of 37% formaldehyde. After refluxing for 1 hour, the solution was cooled to ice bath temperature, treated (portionwise), with 2.5 g of sodium borohydride, and then stirred at ambient temperature for one hour. Evaporation of the volatiles yielded a residue which was taken up in ethyl acetate, washed with water followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. Concentration afforded an oil which was purified by means of high pressure liquid chromatography (silica gel; elution with 10% methanol/dichloromethane) to yield 4.2 g of 1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)piperidine as an oil. The oil which was dissolved in isopropanol and acidified to pH 1 with etheral hydrogen chloride to precipitate 2.34 g (39%) of the corresponding hydrochloride salt, m.p. 151°-153° C.

후처리

  1. temperatureAfter refluxing for 1 hour
  2. temperaturethe solution was cooled to ice bath temperature
  3. customEvaporation of the volatiles
  4. customyielded a residue which
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationConcentration
  8. customafforded an oil which
  9. customwas purified by means of high pressure liquid chromatography (silica gel; elution with 10% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-4ee5be8366c046dcaeac533ab741df12
출처 데이터셋
uspto-grants-1990_04
특허 번호
US04914204

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