Cyanogen Chloride → 1-Cyano-4-benzoyloxy-2,2,6,6-tetramethyl piperidine

HRID 866727ノート

反応式

HRID 866727 の反応式
[C:1]([O:9][CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[N:22]#[C:23]Cl>C(Cl)Cl>[C:23]([N:13]1[C:14]([CH3:17])([CH3:16])[CH2:15][CH:10]([O:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:11][C:12]1([CH3:19])[CH3:18])#[N:22]

参加物

5

反応物 3

HCID 10477Cyanogen ChlorideHCID 14798Sodium HydroxideHCID 5799672,2,6,6-Tetramethyl-4-piperidyl benzoate

生成物 1

HCID 203181911-Cyano-4-benzoyloxy-2,2,6,6-tetramethyl piperidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

104.5 g (0.4 mole) of 4-benzoyloxy-2,2,6,6-tetramethyl piperidine are dissolved in 400 ml of methylene chloride, 400 ml of 1N sodium hydroxide are introduced and 21 ml of cyanogen chloride are added dropwise over a period of 30 minutes with cooling at -5° to -5° C. The cooling is then removed and the mixture is stirred until it reaches room temperature. The organic phase is separated off, dried with sodium sulphate, filtered and the methylene chloride distilled off. Recrystallisation from acetonitrile gives 94 g (82% of the theoretical) of 1-cyano-4-benzoyloxy-2,2,6,6-tetramethyl piperidine melting at 150° to 152° C. The IR-spectrum no longer shows an NH-band, but instead a nitrile band at 2170 cm-1 and a carbonyl band at 1700 cm-1.

後処理

  1. temperaturewith cooling at -5° to -5° C
  2. customThe cooling is then removed
  3. customreaches room temperature
  4. customThe organic phase is separated off
  5. dry with materialdried with sodium sulphate
  6. filtrationfiltered
  7. distillationthe methylene chloride distilled off
  8. customRecrystallisation from acetonitrile

出典と根拠

ORDレコード
ord-fce1ee603c74471aa6a502306e82ca44
出典データセット
uspto-grants-1978_07
特許番号
US04101506

反応ノート

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