Cyanoacetamide → Piperidine

HRID 972682Notes

Reaction equation

HRID 972682 reaction equation
[Na].[N:2]1([C:8]2[CH:18]=[CH:17][C:11]([C:12]([CH2:14][CH:15]=O)=O)=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C[O-].[Na+].N1(C2C=CC(C(=O)C)=CC=2)CCCCC1.C(OCC)=O.[C:42]([CH2:44][C:45]([NH2:47])=[O:46])#[N:43]>C(O)(=O)C.O1CCCC1.O>[NH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[N:2]1([C:8]2[CH:18]=[CH:17][C:11]([C:12]3[NH:47][C:45](=[O:46])[C:44](=[CH:15][CH:14]=3)[C:42]#[N:43])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

11

Reactant 6

HCID 7898CyanoacetamideHCID 8025Ethyl formateHCID 825614'-PiperidinoacetophenoneHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 54217462HCID 54217462, compound

Product 2

HCID 8082PiperidineHCID 214045156-(p-Piperidinophenyl)-1,2-dihydro-2-oxonicotinonitrile

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

From a solution of the sodium salt of p-(piperidino)benzoylacetaldehyde in 300 ml. of water (prepared from 11.4 g. of sodium methoxide in 100 ml. of tetrahydrofuran, and a solution of 36.5 g. of p-(piperidino)acetophenone and 13.3 g. of ethyl formate in 130 ml. of tetrahydrofuran), 18.9 g. of 2-cyanoacetamide and a solution consisting of 2.3 ml. of acetic acid, 5.3 ml. of ester and 4.1 ml. of piperidine, there is obtained 6-(p-piperidinophenyl)-1,2-dihydro-2-oxonicotinonitrile.

Sources & evidence

ORD record
ord-6642e1d4b3834452afa741e2ef8f65c4
Source dataset
uspto-grants-1977_10
Patent number
US04053470

Reaction notes

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