Hydrochloric Acid → Ethyl[{4-[(dodecylamino)carbonyl]benzyl}(piperidin-4-ylmethyl)amino](oxo)acetate hydrochloride

HRID 735837Notes

Reaction equation

[CH2:1]([NH:13][C:14]([C:16]1[CH:44]=[CH:43][C:19]([CH2:20][N:21]([CH2:29][CH:30]2[CH2:35][CH2:34][N:33](C(OC(C)(C)C)=O)[CH2:32][CH2:31]2)[C:22](=[O:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:18][CH:17]=1)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[ClH:45]>C(Cl)Cl.O1CCOCC1>[ClH:45].[CH2:26]([O:25][C:23](=[O:24])[C:22]([N:21]([CH2:20][C:19]1[CH:18]=[CH:17][C:16]([C:14]([NH:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:15])=[CH:44][CH:43]=1)[CH2:29][CH:30]1[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]1)=[O:28])[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of tert-butyl 4-({{4-[(dodecylamino)carbonyl]benzyl}[ethoxy(oxo)acetyl]amino}methyl)piperidine-1-carboxylate (3.84 g, 6.24 mmol) in DCM (25 mL) was added a 4 N solution of HCl in dioxane (31.1 mL) and the resulting reaction mixture was stirred 4 h at 0° C. Evaporation of the solvents gave a white amorphous solid (73%). 1H NMR (DMDO-d6, 300 MHz) δ 9.03 (m, 0.5H), 8.70 (m, 0.5H), 8.50 (m, 1H), 7.85 (m, 2H), 7.33 (m, 2H), 4.56 (d, 2H, J=8.9 Hz), 4.40-4.20 (m, 2H), 3.35-3.10 (m, 7H), 2.80 (m, 2H), 1.70 (m, 2H), 1.52 (m, 2H), 1.43-1.15 (m, 21H), 0.86 (m, 3H). M−(LC/MS(ESI)): 514.4; M+(LC/MS(ESI)): 516.4. HPLC (Condition A), Rt: 4.68 min (HPLC purity: 99.4%).

Workup

customthe resulting reaction mixture
customEvaporation of the solvents

Sources & evidence

ORD record: ord-e1b6aa6c1be040bd97aff2d419c925fa
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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