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

HRID 1031546

反応式

HRID 1031546 の反応式
[F:1][C:2]1[C:20]([F:21])=[C:19]([F:22])[C:18]([F:23])=[C:17]([F:24])[C:3]=1[O:4][C:5]1([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.[CH2:25]=O.[BH4-].[Na+]>CO>[CH3:25][N:8]1[CH2:7][CH2:6][C:5]([O:4][C:3]2[C:17]([F:24])=[C:18]([F:23])[C:19]([F:22])=[C:20]([F:21])[C:2]=2[F:1])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:10][CH2:9]1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 4311764Sodium borohydrideHCID 146499784-(2,3,4,5,6-Pentafluorophenoxy)-4-phenylpiperidine

生成物 1

HCID 148370691-Methyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

To 50 ml of methanol, was added 4.0 g of 4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine and 15 ml of a 37% aqueous formaldehyde solution. After stirring at 70° C. for two hours, the mixture was cooled, and treated (portionwise) with 2.5 g of sodium borohydride over a period of five minutes. After stirring at ambient temperature for two hours, the reaction mixture was evaporated to a semi-solid. The semi-solid was stirred with 50 ml water, then extracted with ethyl acetate. The organic layer was washed with water, followed by a saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. After filtering, evaporation of the solvent yielded a residue which was purified by means of a high pressure liquid chromatography (silica gel, elution with 5% methanol/dichloromethane). The desired fractions were combined, then evaporated to afford 1-methyl-4-(2,3,4,5,6-pentafluorophenoxy)-4-phenylpiperidine as an oil. The oil was dissolved in isopropanol, and acidified to pH 1with etheral-oxalic acid. The resultant precipitate was collected and dried to give 2.5 g (47%), of 1-methyl-4-(2,3,4,5,6-pentaflurophenoxy)-4-phenylpiperidine oxalate, m.p. 152°-154° C. (dec).

後処理

  1. temperaturethe mixture was cooled
  2. stirringAfter stirring at ambient temperature for two hours
  3. customthe reaction mixture was evaporated to a semi-solid
  4. stirringThe semi-solid was stirred with 50 ml water
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtering
  9. customevaporation of the solvent
  10. customyielded a residue which
  11. customwas purified by means of a high pressure liquid chromatography (silica gel, elution with 5% methanol/dichloromethane)
  12. customevaporated

出典と根拠

ORDレコード
ord-054336c59c37439faf5d9e82fc6e02d5
出典データセット
uspto-grants-1990_09
特許番号
US04954511

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