Hydrogen chloride-ethyl acetate → 1-(piperazin-1-yl)-2-[6-(1H-tetrazol-1-yl)pyridin-3-yl]ethanone hydrochloride

HRID 2173319Notes

Reaction equation

HRID 2173319 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH2:12][C:13]([N:15]3[CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[O:14])=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.[ClH:28].CCOC(C)=O>>[ClH:28].[N:15]1([C:13](=[O:14])[CH2:12][C:9]2[CH:10]=[N:11][C:6]([N:1]3[CH:5]=[N:4][N:3]=[N:2]3)=[CH:7][CH:8]=2)[CH2:16][CH2:17][NH:18][CH2:19][CH2:20]1

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 67517595tert-butyl 4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazine-1-carboxylate

Product 1

HCID 675171491-(piperazin-1-yl)-2-[6-(1H-tetrazol-1-yl)pyridin-3-yl]ethanone hydrochloride

Procedure

A mixture of tert-butyl 4-{[6-(1H-tetrazol-1-yl)pyridin-3-yl]acetyl}piperazine-1-carboxylate (60 mg, 0.16 mmol) in HCl/EtOAc (3 mL) was stirred for 3 hours at room temperature. The reaction mixture was concentrated under reduce pressure to give 1-(piperazin-1-yl)-2-[6-(1H-tetrazol-1-yl)pyridin-3yl]ethanone hydrochloride. MS m/z 274 (M+1)+. 1H-NMR (400 MHz, MeOD) δ 9.89 (s, 1H), 8.46 (s, 1H), 8.05˜8.07 (m, 1H), 7.99˜8.00 (m, 1H), 3.99 (s, 2H), 3.85˜3.92 (m, 4H), 3.24˜3.30 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-14462f500ded44e8891034aa71ebdb12
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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