Ammonia → Methyl 4-amino-1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate

HRID 742958Notes

Reaction equation

HRID 742958 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH2:13][C:12](=O)[CH:11]([C:16]([O:18][CH3:19])=[O:17])[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Na+].[Na+].[NH3:26]>C(O)C>[NH2:26][C:12]1[CH2:13][CH2:14][N:9]([CH2:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:10][C:11]=1[C:16]([O:18][CH3:19])=[O:17]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 10340Sodium CarbonateHCID 107479Methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride

Product 1

HCID 563385Methyl 4-amino-1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

855 g of methyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride, 176 g of sodium carbonate and 450 ml of 25% aqueous ammonia solution in 6.5 1 of ethanol were heated for 5 h at an internal temperature of 70° C., with stirring. After concentration under reduced pressure, the mixture was worked up by extraction with dichloromethane and water. The combined dichloromethane phases were dried over sodium sulfate and concentrated under reduced pressure to give 788 g of oily methyl 4-amino-1-benzyl-1,2,5,6-tetrahydropyridine-3-carboxylate as a crude product, which was used in Example 1b) without further purification.

Workup

  1. concentrationAfter concentration under reduced pressure
  2. extractionthe mixture was worked up by extraction with dichloromethane and water
  3. dry with materialThe combined dichloromethane phases were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9e06aeec1ce64a15a8b4388b7277b47c
Source dataset
uspto-grants-1996_09
Patent number
US05556854

Reaction notes

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