Hydrochloric Acid → 1-[(Diphenylmethoxy)acetyl]-3-phenylpiperidine

HRID 1032344ノート

反応式

HRID 1032344 の反応式
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH2:9][C:10](Cl)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]1([CH:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.Cl>C(Cl)Cl.O>[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][CH2:9][C:10]([N:27]2[CH2:28][CH2:29][CH2:30][CH:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 1072073-PhenylpiperidineHCID 13111194(Diphenylmethoxy) acetyl chloride

生成物 1

HCID 145563271-[(Diphenylmethoxy)acetyl]-3-phenylpiperidine収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 4.5 g (17.2 mmole) of (diphenylmethoxy) acetyl chloride in 50 cm3 of methylene chloride was added drop-wise at room temperature to a solution of 2.8 g (17.2 mmole) of 3-phenylpiperidine [prepared according to M. Julia et al., Bull. Soc. Chim. Fr. 1968, 987] and 3.5 g (34.4 mmole) of triethylamine in 100 cm3 of methylene chloride. The reaction mixture was heated to reflux for 4 hours; it was allowed to stand overnight and was then poured into a solution of 10 cm3 of concentrated hydrochloric acid in 300 cm3 of water. The mixture was extracted with methylene chloride, washed with water and dried on sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by silica gel filtration (eluent, hexaneethyl acetate, 1/1), then by recrystallization from a hexane-ethyl acetate mixture. There was obtained 4.3 g (yield: 65%) of 1-[(diphenylmethoxy)acetyl]-3-phenylpiperidine.

後処理

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. extractionThe mixture was extracted with methylene chloride
  4. washwashed with water
  5. customdried on sodium sulfate
  6. customAfter the solvent was evaporated under reduced pressure
  7. filtrationthe residue was purified by silica gel filtration (eluent, hexaneethyl acetate, 1/1)
  8. customby recrystallization from a hexane-ethyl acetate mixture

出典と根拠

ORDレコード
ord-93aaf05872ae490a9d9e9749bfb780d3
出典データセット
uspto-grants-1990_09
特許番号
US04957927

反応ノート

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