1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → HCID 13281208, compound

HRID 364749Notes

Reaction equation

HRID 364749 reaction equation
C(CC[CH:5]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][N:6]1C=O)#N.[C:14]1([CH3:24])[CH:19]=CC(S(O)(=O)=O)=CC=1.[CH2:25]([NH2:28])[CH2:26][NH2:27].[O-]CC.[Na+]>C(O)C>[NH:27]1[CH2:26][CH2:25][N:28]=[C:19]1[CH2:14][CH2:24][CH:9]1[CH2:10][CH2:11][CH2:5][NH:6][CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 2723922Sodium ethoxideHCID 20239762HCID 20239762, compound

Product 1

HCID 13281208HCID 13281208, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture containing 2-cyanoethyl hexahydro-1H-azepine-1-carboxaldehyde (1.94 g, 0.01M) and ethylenediamine p-toluenesulfonate (5.4 g, 0.023M) was heated at 200° C. under nitrogen for 41/2 hrs. The mixture was dissolved in ethanol (30 ml), basified with sodium ethoxide (0.024M), filtered and stripped to dryness. The residue was distilled at 180° to about 190° C., 0.05 mmHg to give rac-4-[2-(4,5-dihydro-1H-imidazol-2-yl)ethyl]hexahydro-1H-azepine (79% yield).

Workup

  1. filtrationfiltered
  2. distillationThe residue was distilled at 180° to about 190° C.

Sources & evidence

ORD record
ord-e0780acf9d97472c8535108d5c4007f7
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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