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

HRID 1458757Notes

Reaction equation

HRID 1458757 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, 0.9913 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. Concentration of the filtrate gave 4-amino-1-methyl-piperidine-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

Sources & evidence

ORD record
ord-5313a4637bfd49229539c3e7075df5ed
Source dataset
uspto-grants-1998_12
Patent number
US05852029

Reaction notes

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