Hydrochloric Acid → (2S)-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]piperidine-2-carboxamide

HRID 857800Notes

Reaction equation

Cl.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:26]2[CH:30]=[N:29][N:28]=[N:27]2)=[C:7]([CH:25]=1)[CH2:8][NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1C(OC(C)(C)C)=O)=[O:11]>CCOC(C)=O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:26]2[CH:30]=[N:29][N:28]=[N:27]2)=[C:7]([CH:25]=1)[CH2:8][NH:9][C:10](=[O:11])[C@@H:12]1[CH2:17][CH2:16][CH2:15][NH:13]1.[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([N:26]2[CH:30]=[N:29][N:28]=[N:27]2)=[C:7]([CH:25]=1)[CH2:8][NH:9][C:10]([C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][NH:13]1)=[O:11]

Participants

Conditions

Temperature: 0 °C

Procedure

HCl gas was bubbled through a cold (0° C.) solution of tert-butyl (2S)-2-({[5-chloro-2-(1H-tetraazol-1-yl)benzyl]amino}carbonyl)piperidine-1-carboxylate (506 mg, 1.20 mmol) in EtOAc (24 mL) for 5 min. The mixture was stirred at 0° C. for 15 min and the solvent was removed in vacuo. Repeated concentration from Et2O afforded the hydrochloride salt of the title compound as a light yellow foam. 1H NMR (400 MHz, CD3OD): δ 9.58 (s, 1 H), 8.71 (br m, 1 H), 7.67 (d, J=2.4 Hz, 1 H), 7.60–7.51 (m, 2 H), 4.34–4.24 (m, 2 H), 3.78 (br m, 1 H), 3.39–3.36 (m, 1 H), 3.03–2.97 (m, 1 H), 2.16–2.13 (m, 1 H), 2.00–1.85 (m, 2 H), 1.70–1.60 (m, 3 H).

Workup

customthe solvent was removed in vacuo
concentrationconcentration from Et2O

Sources & evidence

ORD record: ord-ac217e1cd97e46e5823f21d8f789c985
Source dataset: uspto-grants-2006_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07144899B2

Reaction notes

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