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

HRID 1654490Notes

Reaction equation

HRID 1654490 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 filtrate was neutralized with solid carbon dioxide and the precipitate was removed by filtration. The filtrate was concentrated to a small volume to give 4-amino-1-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 filtrate was concentrated to a small volume

Sources & evidence

ORD record
ord-b6d3eafd24234920899b8ed115361724
Source dataset
uspto-grants-1995_04
Patent number
US05407938

Reaction notes

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