N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea → HCID 54107872, compound

HRID 248978Notes

Reaction equation

HRID 248978 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]([CH2:15][CH2:16][N:17]([CH3:22])[CH2:18][CH2:19][CH2:20][NH2:21])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)=[CH:5][CH:4]=1.[C:25]([NH:27][C:28](=[N:36][CH2:37][CH2:38][CH2:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][N:48]2[CH2:53][CH2:52][CH2:51][CH2:50][CH2:49]2)[CH:42]=1)OC1C=CC=CC=1)#[N:26]>>[C:25]([NH:27][C:28]([NH:21][CH2:20][CH2:19][CH2:18][N:17]([CH2:16][CH2:15][N:8]([CH2:7][C:6]1[CH:23]=[CH:24][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH3:22])=[N:36][CH2:37][CH2:38][CH2:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH2:47][N:48]2[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]2)[CH:42]=1)#[N:26]

Participants

3

Reactant 2

HCID 13486636N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isoureaHCID 19762492HCID 19762492, compound

Product 1

HCID 54107872HCID 54107872, compound

Procedure

Preparation is effected analogously to Example 1, using 0.52 g (1.6 mmol) of N-[2-[N-(4-methoxybenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,3-propanediamine and the equimolar amount of N-cyano-O-phenyl-N'-[3-[3-(piperidinomethyl)phenoxy]propyl]isourea as starting materials. Working up by chromatography analogously to Example 1 yields the purified title compound in the form of a viscous oil which crystallises from absolute ether at -20° C.; MS (+FAB method): m/z (rel. int. [%])=627 ([M+H]+, 6), 241 (11), 121 (100); IR (KBr): 2165 cm-1 (C≡N); m.p.: 62°-65° C. (ether).

Workup

  1. customPreparation
  2. customWorking up by chromatography analogously to Example 1 yields the
  3. custompurified title compound in the form of a viscous oil which
  4. customcrystallises from absolute ether at -20° C.

Sources & evidence

ORD record
ord-112983ec01cd4afa8295c8c2d272751e
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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