Sodium ethoxide → HCID 13281207, compound

HRID 364748Notes

Reaction equation

HRID 364748 reaction equation
[C:1]([CH2:3][CH:4]1[CH2:9][CH2:8][N:7](C=O)[CH2:6][CH2:5]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:23][CH2:24][C:25](N)([CH3:27])[CH3:26].[O-]CC.[Na+]>C(O)C>[CH3:26][C:25]1([CH3:27])[NH:2][C:1]([CH2:3][CH:4]2[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]2)=[N:23][CH2:24]1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 13726734HCID 13726734, compoundHCID 20239790HCID 20239790, compound

Product 1

HCID 13281207HCID 13281207, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
185 °C

Procedure

A mixture containing 4(cyanomethyl)-1-piperidinecarboxaldehyde (3.5 g, 0.023M) and 1,2-diamino-2-methylpropane mono-p-toluenesulfonate (12.4 g, 0.047M) was heated at 185° C. under nitrogen for 5 hrs. The reaction mixture was dissolved in ethanol (20 ml), basified with sodium ethoxide (0.052M), filtered and stripped to dryness. The residue was distilled at 150° C. to about 185° C., 0.02 mmHg, to give (3.1 g, 63%) 4-[(4,5-dihydro-5,5-dimethyl-1H-imidazol-2-yl)methyl]-piperidine.

Workup

  1. filtrationfiltered
  2. distillationThe residue was distilled at 150° C. to about 185° C.

Sources & evidence

ORD record
ord-1a331c8c0f9d45deae66c8c0bc7f745a
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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