Ammonia → 4-Chlorobenzyl-4-[[2-(3-(4-trifluoromethylphenyl)ureido)acetylamino]methyl]piperidine

HRID 279309Notes

Reaction equation

[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH:14][C:15](=[O:18])[CH2:16][NH2:17])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.C1CCNCC1.[F:27][C:28]([F:39])([F:38])[C:29]1[CH:30]=[C:31](N=C=O)[CH:32]=[CH:33][CH:34]=1.N.[N-:41]=[C:42]=[O:43]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH:14][C:15](=[O:18])[CH2:16][NH:17][C:42]([NH:41][C:32]3[CH:33]=[CH:34][C:29]([C:28]([F:27])([F:38])[F:39])=[CH:30][CH:31]=3)=[O:43])[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1-(4-chlorobenzyl)-4-{(glycylamino)methyl}piperidine (14.8 mg, 0.05 mmol) in CHCl3 (2 mL) was treated with (piperidinomethyl)polystyrene resin (28 mg, 2.8 mmol/g), 3-(trifluoromethyl)phenyl isocyanate (1.3 equiv.) and stirred at 25° C. for 16 h. (Aminomethyl)polystyrene was added to scavenge the residual isocyanate and the reaction mixture was stirred at 25° C. for 16 h. Filtration and concentration afforded 1-(4-chlorobenzyl)-4-[{2-(3-(4-trifluoromethylphenyl)ureido)acetylamino}methyl]piperidine (19 mg, 78%) (compound No. 852): The purity was determined by RPLC/MS (92%); ESI/MS m/e 483 (M++H, C23H26ClF3N4O2).

Workup

additionwas added
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-de47e466f4b04f9ba56ba38b666b72dc
Source dataset: uspto-grants-2002_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06362177B1

Reaction notes

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