N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isourea → HCID 54160086, compound

HRID 248985Notes

Reaction equation

HRID 248985 reaction equation
[F:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][N:7]([CH2:14][CH2:15][N:16]([CH3:25])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[C:28]([NH:30][C:31](=[N:39][CH2:40][CH2:41][CH2:42][O:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50][N:51]2[CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[CH:45]=1)OC1C=CC=CC=1)#[N:29]>>[C:28]([NH:30][C:31]([NH:24][CH2:23][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:26]=[CH:27][C:2]([F:1])=[CH:3][CH:4]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)[CH3:25])=[N:39][CH2:40][CH2:41][CH2:42][O:43][C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([CH2:50][N:51]2[CH2:52][CH2:53][CH2:54][CH2:55][CH2:56]2)[CH:45]=1)#[N:29]

Participants

3

Reactant 2

HCID 13486636N-cyano-O-phenyl-N'-[3-(3-(piperidinomethyl)phenoxy]propyl]isoureaHCID 19762519HCID 19762519, compound

Product 1

HCID 54160086HCID 54160086, compound

Procedure

Preparation is effected analogously to Example 1, using 0.48 g (1.3 mmol) of N-[2-[N-(4-fluorobenzyl)-N-(2-pyridyl)amino]ethyl]-N-methyl-1,7-heptanediamine 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. [%])=671 ([M+H]+, 3), 229 (100); IR (KBr): 2164 cm-1 (C≡N). For further analysis, a portion of the compound is converted into the O,O'-ditoluoyltartaric acid salt and recrystallised from isopropanol/ether; m.p.: 96°-98° C. (isopropanol/ether).

Workup

  1. customPreparation
  2. customyields the
  3. custompurified title compound in the form of a viscous oil
  4. customrecrystallised from isopropanol/ether

Sources & evidence

ORD record
ord-33b79f79975e430ba4efa0140b417f20
Source dataset
uspto-grants-1993_05
Patent number
US05212187

Reaction notes

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