Hydrochloric Acid → Arecaidine hydrochloride

HRID 60072Notes

Reaction equation

Br.[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]=[C:5]([C:9]([OH:11])=[O:10])[CH2:4]1.[ClH:12]>>[ClH:12].[CH3:2][N:3]1[CH2:8][CH2:7][CH:6]=[C:5]([C:9]([OH:11])=[O:10])[CH2:4]1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 201453Arecaidine hydrobromide

Product 1

HCID 12305194Arecaidine hydrochloride

Conditions

Temperature: 50 °C

Procedure

1-methyl-1,2,5,6-tetrahydropyridine-3-carboxylate hydrobromide (I-47a, 235 mg, 1.0 mmol) was diluted with concentrated HCl (2.0 mL), and the mixture was heated at 50° C. overnight. The reaction mixture was concentrated in vacuo to afford the title compound (Intermediate 47). MS calculated for C7H12NO2 (M+H+) 142.08. found: 142.1. The crude was used in the next step without further purification.

Workup

concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record: ord-d4fd4b071b23489f834409c472941b56
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440957B2

Reaction notes

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