Cyanoacetamide → Piperidine

HRID 1605926Notes

Reaction equation

HRID 1605926 reaction equation
[Na].[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]([CH2:17][CH:18]=O)=O)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH2:3][CH3:4].C[O-].[Na+].C(N1CCN(C2C=CC(C(=O)C)=CC=2)CC1)CC.C(OCC)=O.[C:48]([CH2:50][C:51]([NH2:53])=[O:52])#[N:49]>O.C(O)(=O)C.O1CCCC1>[NH:8]1[CH2:11][CH2:21][CH2:20][CH2:14][CH2:15]1.[CH2:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:21]=[CH:20][C:14]([C:15]3[NH:53][C:51](=[O:52])[C:50](=[CH:18][CH:17]=3)[C:48]#[N:49])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)[CH2:3][CH3:4]

Participants

11

Reactant 6

HCID 7898CyanoacetamideHCID 8025Ethyl formateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 21404502p-(4-Propyl-1-piperazinyl)acetophenoneHCID 54256791p-(4-Propyl-1-piperazinyl)benzoylacetaldehyde

Product 2

HCID 8082PiperidineHCID 214044896-[p-(4-Propyl-1-piperazinyl)phenyl]-1,2-dihydro-2-oxonicotinonitrile

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

From a solution of the sodium salt of p-(4-propyl-1-piperazinyl)benzoylacetaldehyde in 150 ml. of water (prepared from 5.7 g. of sodium methoxide in 500 ml. of tetrahydrofuran, and a solution of 24.6 g. of p-(4-propyl-1-piperazinyl)acetophenone and 8.0 ml. of ethyl formate in 100 ml. of tetrahydrofuran), 8.4 g. of 2-cyanoacetamide and a solution consisting of 0.95 ml. of acetic acid, 4.0 ml. of water and 0.9 ml. of piperidine, there is obtained 6-[p-(4-propyl-1-piperazinyl)phenyl]-1,2-dihydro-2-oxonicotinonitrile; m.p. 288°-290° (dec.).

Sources & evidence

ORD record
ord-c16ecb7651af4f8ea0e9d0480bf1f424
Source dataset
uspto-grants-1976_04
Patent number
US03951982

Reaction notes

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