Ethyl chloroformate → 1-Ethoxycarbonyl-4-phenoxy-4-phenylpiperidine

HRID 1156031

反応式

HRID 1156031 の反応式
C[N:2]1[CH2:7][CH2:6][C:5]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[CH2:21]([O:23][C:24](Cl)=[O:25])[CH3:22]>>[CH2:21]([O:23][C:24]([N:2]1[CH2:7][CH2:6][C:5]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:4][CH2:3]1)=[O:25])[CH3:22]

参加物

3

反応物 2

HCID 10928Ethyl chloroformateHCID 3060394Piperidine, 1-methyl-4-phenoxy-4-phenyl-

生成物 1

HCID 205366031-Ethoxycarbonyl-4-phenoxy-4-phenylpiperidine

実験手順

9.0 g of 1-methyl-4-phenoxy-4-phenylpiperidine are added in portions of 100 ml of chloroformic acid ethyl ester at 80° C.; severe foaming is observed during this addition. When the addition has ended, the mixture is boiled under reflux for 3 hours, excess chloroformic acid ethyl ester is distilled off in vacuo, and 120 ml of water and 15 ml of concentrated ammonia are added to resulting solid residue. This mixture is stirred thoroughly, and the precipitate is filtered off and rinsed with water. The 1-ethoxycarbonyl-4-phenoxy-4-phenylpiperidine (m.p. 117° to 118° C., from ethanol) thus obtained is boiled under reflux with a solution of 15 g of potassium hydroxide in 150 ml of n-butanol for 4 hours; after cooling, 300 ml of water are added to the solution, and the obtained mixture is extracted twice with diethyl ether. The combined organic phases are dried over sodium sulfate and concentrated. The title compound remains as a brownish oil. The hydrochloride melts at 192° C. (from ethanol).

後処理

  1. additionsevere foaming is observed during this addition
  2. additionWhen the addition
  3. temperatureunder reflux for 3 hours
  4. distillationexcess chloroformic acid ethyl ester is distilled off in vacuo, and 120 ml of water and 15 ml of concentrated ammonia
  5. additionare added
  6. customto resulting solid residue
  7. filtrationthe precipitate is filtered off
  8. washrinsed with water

出典と根拠

ORDレコード
ord-30cf66b11ed94c99813e5bb7aab0b6b6
出典データセット
uspto-grants-1982_06
特許番号
US04333942

関連ノート

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