1-Benzyl-4-piperidone → N~1~-(1-Benzylpiperidin-4-yl)-N~2~-phenylethane-1,2-diamine

HRID 1065243Notes

Reaction equation

HRID 1065243 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([BH3-])#[N:16].[Na+]>CO.Cl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:8][CH2:1][CH2:2][NH:16][C:15]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 192201-Benzyl-4-piperidoneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 20540168N~1~-(1-Benzylpiperidin-4-yl)-N~2~-phenylethane-1,2-diamine

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent2×

Procedure

To the solution of 12.6 g of N-phenylethyleneidamine in 200 ml of methanol, 50 ml of 4.1 N ethanolic hydrogen chloride are added dropwise followed by 18.9 g of 1-benzyl-4-piperidone in 100 ml of methanol. Then, 9.45 g sodium cyanoborohydride are added in portions while stirring at room temperature. After 72 hours the mixture is filtered, the residue dissolved in water and the solution made basic with 12.5% aqueous sodium hydroxide. It is extracted with methylene chloride, dried and evaporated to yield the 1-benzyl-4-(2-phenylaminoethylamino)-piperidine.

Workup

  1. filtrationAfter 72 hours the mixture is filtered
  2. dissolutionthe residue dissolved in water
  3. extractionIt is extracted with methylene chloride
  4. customdried
  5. customevaporated

Sources & evidence

ORD record
ord-f5a14b89fe494cf0bf7c419fb8a15bea
Source dataset
uspto-grants-1982_05
Patent number
US04329348

Reaction notes

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