Potassium Carbonate → 4-Phenyl-1-[3-[3-(trifluoromethyl)phenoxy]-1-azetidinylcarbonyl]piperidine

HRID 1886672

反応式

HRID 1886672 の反応式
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.C(=O)([O-])[O-].[K+].[K+].[C:25]1([CH:31]2[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1.O>[C:25]1([CH:31]2[CH2:32][CH2:33][N:34]([C:11]([N:9]3[CH2:10][CH:7]([O:6][C:5]4[CH:14]=[CH:15][CH:16]=[C:3]([C:2]([F:18])([F:17])[F:1])[CH:4]=4)[CH2:8]3)=[O:12])[CH2:35][CH2:36]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 197996061-Chlorocarbonyl-3-[3-(trifluoromethyl)phenoxy]azetidine

生成物 1

HCID 150533994-Phenyl-1-[3-[3-(trifluoromethyl)phenoxy]-1-azetidinylcarbonyl]piperidine収率 37.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A mixture of 2.8 g (0.01 mole) of 3-[3-(trifluoromethyl)phenoxy]-1-azetidinecarbonyl chloride and 1.4 g (0.01 mole) of potassium carbonate in 25 ml of tetrahydrofuran was stirred for 10 min then treated with 1.6 g (0.01 mole) of 4-phenylpiperidine. After stirring for 30 min, approximately 2 g of ice was added and stirring continued for 18 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml). The extracts were combined, dried and concentrated in vacuo to yield 4.95 g of crude oil which solidified when cooled to -78° C. Recrystallization from isopropyl ether yielded 1.5 g (37%) of coarse white crystals, m.p. 72°-74° C.

後処理

  1. stirringAfter stirring for 30 min
  2. stirringstirring
  3. waitcontinued for 18 hr
  4. customthe oil which separated
  5. extractionwas extracted into methylene chloride (2×50 ml)
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customto yield 4.95 g of crude oil which
  9. customRecrystallization from isopropyl ether

出典と根拠

ORDレコード
ord-7afac462888e4ffe974c6137a2fd52c6
出典データセット
uspto-grants-1992_09
特許番号
US05151418

関連ノート

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