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

HRID 2085390Notes

Reaction equation

HRID 2085390 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-pyridinecarboxyl-ate (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 δ 7.41-7.00 (m, 4 H), 6.10 (br, 1 H), 3.55 (m, 2 H), 3.16 (t, 2 H, J=5.7 Hz), 2.44 (m, 2 H), 2.19 (s, 3 H).

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a733a6021e04cf4bcf9b3d9c5357a2f
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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