Diethylamine → 3-(Pyridin-3-yl)cyclohex-2-en-1-one

HRID 2398980Notes

Reaction equation

N1[CH2:6][CH2:5][O:4]CC1.[NH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.N1[CH2:17][CH2:16][CH2:15][CH2:14]1.C(NCC)C>>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:15]2[CH2:16][CH2:17][CH2:6][C:5](=[O:4])[CH:14]=2)[CH:8]=1

Participants

Reactant 4

HCID 8021Diethylamine

HCID 8082Piperidine

HCID 8083Morpholine

HCID 31268Pyrrolidine

Product 1

HCID 134025713-(Pyridin-3-yl)cyclohex-2-en-1-one

Procedure

Following the procedure described in Example A-2 but using in place of morpholine a molar equivalent quantity of piperidine, pyrrolidine or diethylamine, there is obtained the same final product, 3-(3-pyridinyl)-2-cyclohexen-1-one; however, the following respective intermediates are first produced: 1-(3-pyridinyl)-1-(piperidino)ethylene, 1-(3-pyridinyl)-1-(pyrrolidino)ethylene or 1-(3-pyridinyl)-1-(diethylamino)ethylene and 1-(3-pyridinyl)-3-(piperidino)-1,3-cyclohexadiene, 1-(3-pyridinyl)-3-(pyrrolidino)-1,3-cyclohexadiene or 1-(3-pyridinyl)-3-(diethylamino)-1,3-cyclohexadiene.

Sources & evidence

ORD record: ord-1021d3b33fd445d89d023295a6456b24
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04026900

Reaction notes

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