Hippuric Acid → 4-[(N-benzoylglycyl)amino]methyl-1-(4-chlorobenzyl)piperidine

HRID 133587

Reaktionsgleichung

[C:1]([OH:13])(=O)[CH2:2][NH:3][C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[NH2:42][CH2:43][CH:44]1[CH2:49][CH2:48][N:47]([CH2:50][C:51]2[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=2)[CH2:46][CH2:45]1>ClCCl>[C:4]([NH:3][CH2:2][C:1]([NH:42][CH2:43][CH:44]1[CH2:49][CH2:48][N:47]([CH2:50][C:51]2[CH:52]=[CH:53][C:54]([Cl:57])=[CH:55][CH:56]=2)[CH2:46][CH2:45]1)=[O:13])(=[O:5])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

Hippuric acid (38 mg, 0.21 mmol), EDCI (48 mg, 0.24 mmol), HOBt (31 mg, 0.23 mmol) and triethylamine (38 μL, 0.27 mmol) were added to a dichloromethane (1 mL) solution of 4-(aminomethyl)-1-(4-chlorobenzyl)piperidine (50 mg, 0.21 mmol). The resulting reaction mixture was shaken at 25° C. for 16 hours, then diluted with 1 mL of dichloromethane, washed with a 2 M aqueous solution of NaOH (0.75 mL×2), dried (over MgSO4), concentrated and purified by chromatography (SiO2, 6-8% methanol/dichloromethane) to thereby afford 4-[(N-benzoylglycyl)amino]methyl-1-(4-chlorobenzyl)piperidine (Compd. No. 458). The resulting compound was treated with TFA to provide a TFA salt (105 mg, 97%). The purity was determined by RPLC/MS (85%). ESI/MS m/e 400 (M++H, C22H26ClN3O2).

Aufarbeitung

customThe resulting reaction mixture
washwashed with a 2 M aqueous solution of NaOH (0.75 mL×2)
dry with materialdried (over MgSO4)
concentrationconcentrated
custompurified by chromatography (SiO2, 6-8% methanol/dichloromethane) to thereby afford 4-[(N-benzoylglycyl)amino]methyl-1-(4-chlorobenzyl)piperidine (Compd. No
additionThe resulting compound was treated with TFA

Quellen und Nachweise

ORD-Eintrag: ord-417eb02fb1774d4c84ec57fe787b3474
Quelldatensatz: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07390830B1

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