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

HRID 866727Notes

Reaction equation

HRID 866727 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fce1ee603c74471aa6a502306e82ca44
Source dataset
uspto-grants-1978_07
Patent number
US04101506

Reaction notes

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