Methanol → HCID 23035496, compound

HRID 2118983Notes

Reaction equation

[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:21][OH:22].C(Cl)(Cl)[Cl:24]>>[ClH:24].[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:18]=[CH:19][CH:20]=2)[O:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16](=[NH:17])[O:22][CH3:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 3

HCID 887Methanol

HCID 6212Chloroform

HCID 23035478HCID 23035478, compound

Product 1

HCID 23035496HCID 23035496, compound

Conditions

Temperature: 0 °C

Procedure

5-[3-(Piperidinomethyl)phenoxy]pentanenitrile (1.73 g was dissolved in chloroform (20 ml). This solution was cooled to 0° C., which was followed by the addition of methanol (0.81 g). Dry hydrogen chloride gas was bubbled into the solution for 3 hours, which was then stored at 0° C. overnight. Chloroform was removed under reduced pressure to leave as an oily residue methyl 5-[3-(piperidinomethyl)phenoxy]pentaneimidate hydrochloride (1.3 g) which was not isolated. This was taken up in ethanol (20 ml) followed by the addition of orthophenylenediamine (0.41 g) and stirred at room temperature for 2 hours. Ethanol was removed under reduced pressure to leave an oily residue which was taken up in water, neutralised with potassium carbonate and extracted into chloroform (3×50 ml) and dried over magnesium sulphate, filtered, evaporated to low volume under reduced pressure and subjected to medium pressure liquid chromatography (ethyl acetate) to afford the title compound as a solid, m.p. 130°-131° C. (recrystallised from ethyl acetate).

Workup

customDry hydrogen chloride gas was bubbled into the solution for 3 hours
customChloroform was removed under reduced pressure

Sources & evidence

ORD record: ord-1968c87c40d94ad680c1e8072889ba58
Source dataset: uspto-grants-1987_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04681883

Reaction notes

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