HCID 20192806, compound → HCID 86741665, compound

HRID 2118640Notes

Reaction equation

HRID 2118640 reaction equation
[C:1]1([CH2:7][C:8]#[C:9][N:10]([CH3:22])[CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[H][H]>N1C=CC=CC=1>[C:1]1([CH2:7]/[CH:8]=[CH:9]\[N:10]([CH3:22])[CH2:11][C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 20192806HCID 20192806, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86741665HCID 86741665, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineCatalyst

Procedure

5 g of N-(3cyclohex-1-en-1-yl-propynyl)-N-methyl-N-(1-naphthylmethyl)amine are hydrogenated in absolute pyridine using 750 mg Pd/BaSO4 as catalyst at room temperature and normal pressure, until the calculated amount of hydrogen is taken up. The reaction mixture is filtered and the pyridine removed in a vacuum. The residue is chromatographed on silica-gel using benzene/ethylacetate (9:1) to yield the title compound in free base form as an oil after evaoporating the appropriate fractions,

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe pyridine removed in a vacuum
  3. customThe residue is chromatographed on silica-gel

Sources & evidence

ORD record
ord-560b40c35afb4f7cb0a22207d21b566e
Source dataset
uspto-grants-1987_07
Patent number
US04680291

Reaction notes

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