1,2-Ethanediamine, 4-methylbenzenesulfonate (1:?) → 4-[3-(4,5-dihydro-1H-imidazol-2-yl)propyl]piperidine

HRID 364710Notes

Reaction equation

HRID 364710 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH:6]1[CH2:11][CH2:10][N:9](C=O)[CH2:8][CH2:7]1)#[N:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:25](N)[CH2:26][NH2:27].CO[Na]>C(O)C>[NH:27]1[CH2:26][CH2:25][N:2]=[C:1]1[CH2:3][CH2:4][CH2:5][CH:6]1[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 202397594-(3-Cyanopropyl)-1-piperidinecarboxaldehydeHCID 178418582HCID 178418582, compound

Product 1

HCID 132811894-[3-(4,5-dihydro-1H-imidazol-2-yl)propyl]piperidineYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

To 4-(3-cyanopropyl)-1-piperidinecarboxaldehyde (10 g, 0.055M), there was added ethylenediamine p-toluenesulfonate (30 g, 0.129M) and the mixture was heated at 200° C. for 41/2 hours. The reaction mixture was dissolved in ethanol (100 ml), basified with MeONa (0.26M), filtered and stripped to dryness. The residue was distilled at 170° C., 0.025 mmHg to give 4-[3-(4,5-dihydro-1H-imidazol-2-yl)propyl]piperidine (7.86 g, 72% yield).

Workup

  1. filtrationfiltered
  2. distillationThe residue was distilled at 170° C.

Sources & evidence

ORD record
ord-1f60c9de2e66477588ee22b0a41547e8
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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