HCID 85370880, compound → 2-(2-Aminophenethyl)-1-methylpiperidine

HRID 653197Notes

Reaction equation

HRID 653197 reaction equation
COS([O-])(=O)=O.[N+:7]([C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N+:15]=1[CH3:20])([O-])=O.[H][H]>C(O)C.[Pt]>[NH2:7][C:10]1[CH:24]=[CH:23][CH:22]=[CH:21][C:11]=1[CH2:12][CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][N:15]1[CH3:20]

Participants

5

Reactant 2

HCID 85370880HCID 85370880, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 110852822-(2-Aminophenethyl)-1-methylpiperidineYield 93.6%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

2-(2-Nitrostyrenyl)-1-methylpyridinium methyl sulfate (III; 25 g, 0.07 moles) and 10 g of 5% Pt on carbon (50% water wet) in 300 mL of 95% ethanol was put in a 2L Parr hydrogenation flask and hydrogenated at approximately 2 psi of hydrogen for 16 hours. The hydrogenation mixture rapidly turned orange and then slowly became colorless as the organic solid dissolved. Catalyst was removed by filtration and held for subsequent runs. The filtrate was concentrated in vacuo to an oil which was dissolved in 50 mL water and made basic (pH~11) with 50% sodium hydroxide solution. The basic aqueous phase was extracted with 50 and 25 mL portions of methylene chloride, the extracts were combined and dried (anhyd. K2CO3) , filtered and the solid removed in vacuo to yield 14.3 g (92%) of product II as an amber oil. This intermediate diamine oil (cf: U.S. 3,931,195; Example 1) was used directly in the next step of the process.

Workup

  1. dissolutionThe hydrogenation mixture rapidly turned orange and then slowly became colorless as the organic solid dissolved
  2. customCatalyst was removed by filtration
  3. concentrationThe filtrate was concentrated in vacuo to an oil which
  4. dissolutionwas dissolved in 50 mL water
  5. extractionThe basic aqueous phase was extracted with 50 and 25 mL portions of methylene chloride
  6. dry with materialdried (anhyd. K2CO3)
  7. filtrationfiltered
  8. customthe solid removed in vacuo

Sources & evidence

ORD record
ord-18265cd3d6d040e8911f4bb4d9ae53e3
Source dataset
uspto-grants-1987_06
Patent number
US04675409

Reaction notes

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