1,3,8-Triazaspiro(4.5)decane-2,4-dione, 8-methyl- → 4-Amino-1-methylpiperidine-4-carboxylic acid

HRID 1734560Notes

Reaction equation

HRID 1734560 reaction equation
[CH3:1][N:2]1[CH2:13][CH2:12][C:5]2([NH:9]C(=O)N[C:6]2=[O:11])[CH2:4][CH2:3]1.[OH2:14].O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>O>[NH2:9][C:5]1([C:6]([OH:11])=[O:14])[CH2:4][CH2:3][N:2]([CH3:1])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 23022601,3,8-Triazaspiro(4.5)decane-2,4-dione, 8-methyl-HCID 17749109Barium hydroxide, octahydrate

Product 1

HCID 2729544-Amino-1-methylpiperidine-4-carboxylic acidYield 379.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-Methylpiperidine-4-spiro-5'-hydantoin (9.75 g, 0.0533 mole) and barium hydroxide octahydrate (28.8 g, 0.0913 mole) in water (150 ml) were heated at 160° C. in a bomb for 3 hr. The content of four such batches were combined and the precipitated barium carbonate was filtered off. The filtrate was neutralized with solid CO2 and the precipitate removed by filtration. The filtrate was concentrated to give 4-amino-1-methylpiperidine-4-carboxylic acid (32.0 g., 95%) mp. 275°-280° C. (dec.).

Workup

  1. filtrationthe precipitated barium carbonate was filtered off
  2. customthe precipitate removed by filtration
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8ca3b7d6988948eaa0d60a00f9163b9b
Source dataset
uspto-grants-1996_07
Patent number
US05534520

Reaction notes

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