1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 18426157, compound

HRID 133579Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:12]=[CH:13][CH:14]=1)[C:5]([NH:7][CH2:8][C:9]([OH:11])=O)=[O:6].CCN=C=NCCCN(C)C.O.ON1C2C=CC=CC=2N=N1.Cl.Cl.[Cl:39][C:40]1[CH:53]=[CH:52][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH2:48][CH:47]([NH2:51])[CH2:46]2)=[CH:42][CH:41]=1>C(N(CC)CC)C.C(Cl)(Cl)Cl>[Cl:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH2:48][CH:47]([NH:51][C:9](=[O:11])[CH2:8][NH:7][C:5](=[O:6])[C:4]3[CH:12]=[CH:13][CH:14]=[C:2]([CH3:1])[CH:3]=3)[CH2:46]2)=[CH:52][CH:53]=1

Participants

Conditions

Temperature: 25 °C

Procedure

N-(3-Methylbenzoyl)glycine (10.6 mg, 0.055 mmol), EDCI (10.5 mg) and 1-hydroxybenzotriazole hydrate (7.4 g) were added to a chloroform (2.5 mL) solution of 1-(4-chlorobenzyl)-3-aminopiperidine dihydrochloride (1.49 mg, 0.050 mmol) and triethylamine (15.2 mg). The resulting reaction mixture was stirred at 25° C. for 16 hours and washed with a 2 N aqueous solution of NaOH (2 mL×2) and brine (1 mL). After filtration through a PTFE membrane, the solvent was removed under reduced pressure to provide 1-(4-chlorobenzyl)-3-[[N-(3-methylbenzoyl)glycyl]amino]piperidine (Compd. No. 355) (17.4 mg, 87%). The purity was determined by RPLC/MS (97%). ESI/MS m/e 400.0 (M++H, C22H26ClN3O2).

Workup

customThe resulting reaction mixture
washwashed with a 2 N aqueous solution of NaOH (2 mL×2) and brine (1 mL)
filtrationAfter filtration through a PTFE membrane
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-36bc6d735c184947be9b4ed60c760738
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390830B1

Reaction notes

Loading…