Cyanoacetamide → Saterinone

HRID 1249374Notes

Reaction equation

HRID 1249374 reaction equation
CN(C)[CH:3]=[C:4]([C:8]1[CH:32]=[CH:31][C:11]([O:12][CH2:13][CH:14]([OH:30])[CH2:15][N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])[CH2:18][CH2:17]2)=[CH:10][CH:9]=1)[C:5](=O)[CH3:6].C(=O)([O-])[O-].[K+].[K+].[C:40]([CH2:42][C:43]([NH2:45])=[O:44])#[N:41]>C(#N)C.S(=O)(=O)(O)[O-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:40]([C:42]1[C:43](=[O:44])[NH:45][C:5]([CH3:6])=[C:4]([C:8]2[CH:32]=[CH:31][C:11]([O:12][CH2:13][CH:14]([OH:30])[CH2:15][N:16]3[CH2:17][CH2:18][N:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[O:28][CH3:29])[CH2:20][CH2:21]3)=[CH:10][CH:9]=2)[CH:3]=1)#[N:41]

Participants

6

Reactant 3

HCID 7898CyanoacetamideHCID 11430Potassium CarbonateHCID 54471454HCID 54471454, compound

Product 1

HCID 65874SaterinoneYield 23.4%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 6342AcetonitrileSolvent

Procedure

9.0 g of 1-[4-(4-dimethylamino-3-buten-2-on-3-yl)-phenoxy]-3-[4-(2-methoxyphenyl)-piperazin-1-yl]-propan2-ol are heated under reflux in 100 ml of acetonitrile with 5.66 g of potassium carbonate, 0.67 g of tetrabutylammonium bisulphate and 2.52 g of cyanoacetamide for 36 hours. The solvent is then distilled off in vacuo, the residue is dissolved in 50 ml of water and the solution is neutralised with dilute hydrochloric acid and extracted several times with ethyl acetate. The extracts are dried and concentrated. The residue is purified by column chromatography on silica gel (chloroform:methanol=10:1). 2.2 g of 1-[4-(3-cyano-1,2-dihydro-6-methyl-2-oxo-pyridin-5-yl)-penoxy]-3-[4-(2-methoxyphenyl)-piperazin-1-yl]-propan-2-ol are obtained.

Workup

  1. distillationThe solvent is then distilled off in vacuo
  2. dissolutionthe residue is dissolved in 50 ml of water
  3. extractionextracted several times with ethyl acetate
  4. customThe extracts are dried
  5. concentrationconcentrated
  6. customThe residue is purified by column chromatography on silica gel (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-ab11b9533bc543bbad3e091fd5cea7d2
Source dataset
uspto-grants-1986_12
Patent number
US04631281

Reaction notes

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