N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea → HCID 53971387, compound

HRID 248984Notes

Reaction equation

HRID 248984 reaction equation
[F:1][C:2]1[CH:26]=[CH:25][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH2:23])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:27]([NH:29][C:30](=[N:38][CH2:39][CH2:40][CH2:41][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49][N:50]2[CH2:55][CH2:54][CH2:53][CH2:52][CH2:51]2)[CH:44]=1)OC1C=CC=CC=1)#[N:28]>>[C:27]([NH:29][C:30]([NH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][N:7]([CH2:6][C:5]1[CH:25]=[CH:26][C:2]([F:1])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:24])=[N:38][CH2:39][CH2:40][CH2:41][O:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49][N:50]2[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55]2)[CH:44]=1)#[N:28]

Participants

3

Reactant 2

HCID 13486636N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isoureaHCID 19762604HCID 19762604, compound

Product 1

HCID 53971387HCID 53971387, compound

Procedure

Preparation is effected analogously to Example 1, using 0.33 g (0.9 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,6-hexanediamine and the equimolar amount of N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea as starting materials. Chromatographic working-up analogously to Example 1 yields the purified title compound in the form of a viscous oil; MS (+FAB method): m/z (rel. int. [%])=657 ([M+H]+, 11), 229 (100); IR (KBr): 2164 cm-1 (C≡N). For further analysis, a portion of the compound is converted into the tartaric acid salt in an ethanol/ether solvent mixture; m.p.: 58° C. (ethanol/ether).

Workup

  1. customPreparation
  2. customyields the
  3. custompurified title compound in the form of a viscous oil

Sources & evidence

ORD record
ord-2db6e9ed7af84cd9a4729b0905b6f164
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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