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

HRID 133599Notes

Reaction equation

C1CCNCC1.[F:7][C:8]([F:19])([F:18])[C:9]1[CH:10]=[C:11](N=C=O)[CH:12]=[CH:13][CH:14]=1.[Cl:20][C:21]1[CH:39]=[CH:38][C:24]([CH2:25][N:26]2[CH2:31][CH2:30][CH:29]([CH2:32][NH:33][C:34](=[O:37])[CH2:35][NH2:36])[CH2:28][CH2:27]2)=[CH:23][CH:22]=1.N.[N-:41]=[C:42]=[O:43]>C(Cl)(Cl)Cl>[Cl:20][C:21]1[CH:39]=[CH:38][C:24]([CH2:25][N:26]2[CH2:27][CH2:28][CH:29]([CH2:32][NH:33][C:34](=[O:37])[CH2:35][NH:36][C:42]([NH:41][C:12]3[CH:13]=[CH:14][C:9]([C:8]([F:7])([F:18])[F:19])=[CH:10][CH:11]=3)=[O:43])[CH2:30][CH2:31]2)=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A (piperidinomethyl)polystyrene resin (28 mg, 2.8 mmol/g) and 3-(trifluoromethyl)phenyl isocyanate (1.3 equivalents) were added to a chloroform (2 mL) solution of 1-(4-chlorobenzyl)-4-[(glycylamino)methyl]piperidine (14.8 mg, 0.05 mmol). The resulting mixture was stirred at 25° C. for 16 hours, and an (aminomethyl)polystyrene resin was added to the obtained mixture. The resulting mixture was stirred at 25° C. for 16 hours to trap the remaining isocyanate. The obtained mixture was filtered and concentrated to thereby provide 1-(4-chlorobenzyl)-4-[[2-(3-(4-trifluoromethylphenyl)ureido) acetylamino]methyl]piperidine (Comp d. No. 852) (19 mg, 78%). The purity was determined by RPLC/MS (92%). ESI/MS m/e 483 (M++H, C23H26ClF3N4O2).

Workup

filtrationThe obtained mixture was filtered
concentrationconcentrated to thereby provide 1-(4-chlorobenzyl)-4-[[2-(3-(4-trifluoromethylphenyl)ureido) acetylamino]methyl]piperidine (Comp

Sources & evidence

ORD record: ord-fa8d1e61e8c842c3b28f85b84cb1c0c5
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390830B1

Reaction notes

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