Ethanol → Ethyl 1-Benzyl-4-(3-methylphenylamino)-piperidine-4-carboxylate

HRID 565604Notes

Reaction equation

HRID 565604 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:30](O)[CH3:31]>>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[CH:19]=2)([C:14]([O:16][CH2:30][CH3:31])=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 211934454-(m-Toluidino)-1-benzylpiperidine-4-carboxylic acid

Product 1

HCID 21193210Ethyl 1-Benzyl-4-(3-methylphenylamino)-piperidine-4-carboxylate

Procedure

A mixture of 1-benzyl-4-(3-methylphenylamino)piperidine-4-carboxylic acid (3.81 g, 11.7 mmol) and concentrated sulfuric acid (2 mL) in absolute ethanol (80 mL) was heated under reflux overnight. The resultant solution was concentrated under vacuum, and the residue was treated with chloroform saturated with ammonia gas. The mixture was filtered, and the filtrate concentrated. The residue was passed through a small plug of silica gel eluting with chloroform saturated with ammonia gas. Collection and concentration of the eluent under vacuum provided the title compound.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. concentrationThe resultant solution was concentrated under vacuum
  4. additionthe residue was treated with chloroform saturated with ammonia gas
  5. filtrationThe mixture was filtered
  6. concentrationthe filtrate concentrated
  7. customCollection and concentration of the eluent under vacuum

Sources & evidence

ORD record
ord-be1358e429ca468293c75bd6c80c0f1a
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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