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

HRID 866726Notes

Reaction equation

HRID 866726 reaction equation
[OH:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[NH:5][C:4]([CH3:11])([CH3:10])[CH2:3]1.[OH-].[Na+].[N:14]#[C:15]Cl>C(Cl)Cl.O>[C:15]([N:5]1[C:4]([CH3:11])([CH3:10])[CH2:3][CH:2]([OH:1])[CH2:7][C:6]1([CH3:9])[CH3:8])#[N:14]

Participants

6

Reactant 3

HCID 10477Cyanogen ChlorideHCID 14798Sodium HydroxideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidine

Product 1

HCID 203033451-Cyano-4-hydroxy-2,2,6,6-tetramethyl piperidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

62.8 g (0.4 mole) of 4-hydroxy-2,2,6,6-tetramethyl piperidine are dissolved in 250 ml of methylene chloride a solution of 16 g (0.4 mole) of sodium hydroxide in 250 ml of water is introduced and 20.5 ml of cyanogen chloride are added dropwise to the mixture at 0° to 5° C. The mixture is stirred until it reaches room temperature, after which the organic phase is separated off, dried with sodium sulphate, filtered and the methylene chloride distilled off, leaving 31 g (42.5% of the theoretical) of 1-cyano-4-hydroxy-2,2,6,6-tetramethyl piperidine. Bp 0.5 = 135° C; melting point 96°-98° C.

Workup

  1. additionis introduced
  2. customreaches room temperature
  3. customafter which the organic phase is separated off
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. distillationthe methylene chloride distilled off

Sources & evidence

ORD record
ord-7afc958b19654dae80b63053fd95f940
Source dataset
uspto-grants-1978_07
Patent number
US04101506

Reaction notes

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