1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → HCID 13281188, compound

HRID 364708Notes

Reaction equation

HRID 364708 reaction equation
[C:1]([CH2:3][CH2:4][CH:5]1[CH2:10][CH2:9][N:8](C=O)[CH2:7][CH2:6]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](N)[CH2:25][NH2:26]>>[NH:26]1[CH2:25][CH2:24][N:2]=[C:1]1[CH2:3][CH2:4][CH:5]1[CH2:6][CH2:7][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 2

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 13726735HCID 13726735, compound

Product 1

HCID 13281188HCID 13281188, compound

Conditions

Temperature
200 °C

Procedure

A mixture containing 4-(2-cyanoethyl)-1-piperidinecarboxaldehyde (10 g, 0.06M) and ethylenediamine p-toluenesulfonate (30 g, 0.129M) were heated at 200° C. for 41/2 hours. Crystallization of the crude reaction mixture from isopropanol (70 ml) yielded the desired product as the di-p-toluenesulfonate salt (14 g). The salt was then basified with 2 equivalents of MeONa and distilled (0.2 mmHg, 170° C.) to give 4-[2-(4,5-dihydro-1H-imidazol-2-yl)ethyl]piperidine (4.1 g, 37% yield).

Workup

  1. customCrystallization of the crude
  2. customreaction mixture from isopropanol (70 ml)

Sources & evidence

ORD record
ord-64a72fcaccf5474e8d0edcf83503af57
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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