Cyanogen Chloride → HCID 85891174, compound

HRID 866725Notes

Reaction equation

HRID 866725 reaction equation
[NH2:1][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>[NH:1]([CH:2]1[CH2:3][C:4]([CH3:11])([CH3:10])[NH:5][C:6]([CH3:9])([CH3:8])[CH2:7]1)[C:15]#[N:14]

Participants

6

Reactant 3

HCID 10477Cyanogen ChlorideHCID 14798Sodium HydroxideHCID 375244-Amino-2,2,6,6-tetramethylpiperidine

Product 1

HCID 85891174HCID 85891174, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

156 g (1 mole) of 4-amino-2,2,6,6-tetramethyl piperidine are dissolved in 500 ml of methylene chloride, 40 g (1 mole) of sodium hydroxide in 500 ml of water are introduced and 51 ml of cyanogen chloride are added dropwise at a temperature of 0° to 5° C. The mixture is stirred until it reaches room temperature, after which 4-cyanamido-2,2,6,6-tetramethyl piperidine, which melts at 240° C, is filtered off in a yield of 166 g (corresponding to 91.5% of the theoretical).

Workup

  1. customreaches room temperature
  2. filtrationafter which 4-cyanamido-2,2,6,6-tetramethyl piperidine, which melts at 240° C, is filtered off in a yield of 166 g (corresponding to 91.5% of the theoretical)

Sources & evidence

ORD record
ord-bbf6c9f5754b45d39409d367cc4cb751
Source dataset
uspto-grants-1978_07
Patent number
US04101506

Reaction notes

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