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

HRID 2187809Notes

Reaction equation

[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:5][CH2:4]1.[C:17](O)(=[O:28])[CH2:18][NH:19][C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:21].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(CC)CC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:20]([NH:19][CH2:18][C:17]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[CH2:5][CH2:4]1)=[O:28])(=[O:21])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4-(aminomethyl)-1-(4-chlorobenzyl)piperidine (50 mg, 0.21 mmol) in CH2Cl2 (1 mL) was treated with hippuric acid (38 mg, 0.21 mmol), EDCI (48 mg, 0.24 mmol), HOBt (31 mg, 0.23 mmol) and Et3N (38 μL, 0.27 mmol). The reaction mixture was stirred for 16 h at 25° C., diluted with 1 mL of CH2Cl2, washed with 2 N aqueous NaOH solution (2×0.75 mL), dried (MgSO4) and concentrated. Chromatography (SiO2, 6 to 8% CH3OH/CH2Cl2 gradient elution) afforded 4-{(N-benzoylglycyl)amino)methyl-1-(compound No. 458) which was treated with TFA to give a TFA salt(105 mg, 97%): The purity was determined by RPLC/MS (85%); ESI/MS m/e 400 (M++H, C22H26ClN3O2)

Workup

washwashed with 2 N aqueous NaOH solution (2×0.75 mL)
dry with materialdried (MgSO4)
concentrationconcentrated
washChromatography (SiO2, 6 to 8% CH3OH/CH2Cl2 gradient elution)
customafforded 4-{(N-benzoylglycyl)amino)methyl-1-(compound No

Sources & evidence

ORD record: ord-5a2dc793a2224f05a62d9771fb1d8491
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06410566B1

Reaction notes

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