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

HRID 1734568Notes

Reaction equation

HRID 1734568 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 2,215.5%

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., 0.00913 mole) in water (150 ml.) were heated at 160° C. in an autoclave for three hours. The contents of four such batches were combined and the precipitated barium carbonate was filtered off. The liltrate was neutralized with solid carbon dioxide and the precipitate was removed by filtration. The liltrate was concentrated to a small volume to give 4-amino-l-methylpiperidine-4-carboxylic acid (32.0 g., 95% yield), m.p. 275°-280° C. (dec.).

Workup

  1. filtrationthe precipitated barium carbonate was filtered off
  2. customthe precipitate was removed by filtration
  3. concentrationThe liltrate was concentrated to a small volume

Sources & evidence

ORD record
ord-ea19af42e33d4c29990d6b309f91dfe5
Source dataset
uspto-grants-1996_07
Patent number
US05534520

Reaction notes

Loading…