Hydrochloric Acid → N-(3-(1,2,3,6-Tetrahydropyridin-4-yl)phenyl)acetamide

HRID 2087128Notes

Reaction equation

HRID 2087128 reaction equation
Cl.[C:2]([NH:5][C:6]1[CH:7]=[C:8]([C:12]2[CH2:13][CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH:17]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:4])[CH3:3]>O1CCOCC1.ClCCl>[NH:15]1[CH2:14][CH:13]=[C:12]([C:8]2[CH:7]=[C:6]([NH:5][C:2](=[O:4])[CH3:3])[CH:11]=[CH:10][CH:9]=2)[CH2:17][CH2:16]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 219571881,1-Dimethylethyl 4-[3-(acetylamino)phenyl]-3,6-dihydro-1(2H)-pyridinecarboxylate

Product 1

HCID 21957228N-(3-(1,2,3,6-Tetrahydropyridin-4-yl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 4 M HCl in dioxane (10 mL) was added to tert-butyl 4-[3-(acetylamino)phenyl]-1,2,3,6-tetrahydro-1-pyridinecarboxylate (8.25 mmol) in dichloromethane (30 mL). The reaction mixture was stirred at room temperature overnight, concentrated in vacuo, giving the desired product as the hydrochloride salt (2.1 g): 1H NMR (CDCl3) δ 7.41-7.00 (m, 4H), 6.10 (br, 1H), 3.55 (m, 2H), 3.16 (t, 2H, J=5.7 Hz), 2.44 (m, 2H), 2.19 (s, 3H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af27fa73124e489dafad95a43fdaf7b6
Source dataset
uspto-grants-2004_04
Patent number
US06727264B1

Reaction notes

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