1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(4-Chlorobenzyl)-3-[(4-benzoylbutyryl)amino]homopiperidine

HRID 133629

Reaction equation

CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:22][CH:23]1[CH2:29][CH2:28][CH2:27][CH2:26][N:25]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)[CH2:24]1.[C:38]([CH2:46][CH2:47][CH2:48][C:49](O)=[O:50])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>ClCCl.C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][N:25]2[CH2:26][CH2:27][CH2:28][CH2:29][CH:23]([NH:22][C:49](=[O:50])[CH2:48][CH2:47][CH2:46][C:38](=[O:45])[C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[CH2:24]2)=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 25 °C

Procedure

EDCI (23 mg), HOBt (16.2 mg) and triethylamine (15.2 μL) were added to a chloroform (1 mL) solution of 3-amino-1-(4-chlorobenzyl)homopiperidine (24 mg, 0.10 mmol) and 4-benzoylbutyric acid (1.2 equivalents), and the resulting mixture was stirred at 25° C. for 16 hours. The reaction mixture was diluted with dichloromethane (0.5 mL), filtered through a PTFE membrane and concentrated to provide 1-(4-chlorobenzyl)-3-[(4-benzoylbutyryl)amino]homopiperidine (Compd. No. 994) (43 mg, 99%). The purity was determined by RPLC/MS (98%). ESI/MS m/e 413 (M++H, C24H29ClN2O2).

Workup

filtrationfiltered through a PTFE membrane
concentrationconcentrated

Sources & evidence

ORD record: ord-dba731bce0ea47c6ab606634cae1e2a4
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390830B1

Linked notes

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