Hydrochloric Acid → (+)-4-[(4-Fluorophenoxy)phenyl]methyl-piperidine

HRID 1058781

反応式

HRID 1058781 の反応式
[C:1]1([CH:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C([O-])(=[O:24])C1C=CC=CC=1.[K+].[F:27][C:28]1[CH:33]=[CH:32][C:31](F)=[CH:30][CH:29]=1.[Na+].[Cl-].Cl>CS(C)=O.CO.O>[F:27][C:28]1[CH:33]=[CH:32][C:31]([O:24][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[CH2:7][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:30][CH:29]=1

参加物

10

反応物 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 108921,4-DifluorobenzeneHCID 24758Sodium hydrideHCID 339086Phenyl-piperidin-4-yl-methanolHCID 23661960Potassium Benzoate

生成物 1

HCID 18669358(+)-4-[(4-Fluorophenoxy)phenyl]methyl-piperidine収率 64%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒2 回HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
72.5 °C

実験手順

The alcohol prepared above (1.3 g, 4.5 mmol) dissolved in DMSO (10 mL) was added over an NaH (60%, 210 g) suspension in DMSO (5 mL). Potassium benzoate (715 g, 4.5 mmol) and 1,4-difluorobenzene (0.75 mL, 6.86 mmol) were added and the mixture heated (70-75° C.) until the starting substance disappeared. The reaction mixture was poured into water and saturated aqueous NaCl solution, and extracted with ether. The oil obtained was refluxed with a mixture of methanol (17 mL) and an aqueous hydrochloric acid (17 mL) solution for 1 h. The usual working of the reaction provided (−)-4-[(4-fluorophenoxy)phenyl]methyl-piperidine as an oil in a 64% yield. Treatment of this oil with L-dibenzoyltartaric acid in ethanol (96%, 35 mL) provided a precipitate which was filtered (m.p.=193-194° C.). The aminoether was released yielding a white solid with a 98% ee, m.p.=100-102° C., and [α]546−14, c=0.2, CHCl3).

後処理

  1. extractionextracted with ether
  2. customThe oil obtained

出典と根拠

ORDレコード
ord-bf4a815c6602482ab51787f9371fd8ff
出典データセット
uspto-grants-2003_02
特許番号
US06518284B2

関連ノート

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