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

HRID 2072804ノート

反応式

HRID 2072804 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4ee5be8366c046dcaeac533ab741df12
出典データセット
uspto-grants-1990_04
特許番号
US04914204

反応ノート

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