Compound: Triacetonamine
SMILES: O=C1CC(NC(C1)(C)C)(C)C
InChIKey: JWUXJYZVKZKLTJ-UHFFFAOYSA-N
Synonyms: Triacetonamine, 826-36-8, 2,2,6,6-Tetramethyl-4-piperidone, Vincubine, Tempidon, TMPone, DTXSID4041527, 2K4430S3XP, NSC-16579, IKH-19, DTXCID2021527, RefChem:891346, 2,2,6,6-tetramethylpiperidone-4-toluene-p-sulfonate, 212-554-2, 2,2,6,6-tetramethylpiperidin-4-one, Triacetonamin, 2,2,6,6-Tetramethyl-4-piperidinone, Triacetone amine, Vincubina, 2,2,6,6-Tetramethyl-4-oxopiperidine, 4-Piperidinone, 2,2,6,6-tetramethyl-, Trojacetonoaminy, 2,2,6,6-Tetramethylpiperidone, Odoratine, 4-Oxo-2,2,6,6-tetramethylpiperidine, 2,2,6,6-Tetramethylpiperidinone, Triacetoneamine, 2,2,6,6-Tetramethyl-piperidin-4-one, NSC 16579, 4-Oxo-2,2,6,6-tetramethyl-4-piperidone, 4-PIPERIDONE, 2,2,6,6-TETRAMETHYL-, MFCD00005975, 4-OXO-2,2,6,6-TETRAMETHYLPIPERIDINE (D17, 15N), Trojacetonoaminy [Polish], Tetramethylpiperidinone, EINECS 212-554-2, BRN 0112665, UNII-2K4430S3XP, Odoratin?, EC 212-554-2, Ikh 196, Oprea1_386573, SCHEMBL38953, 5-21-06-00538 (Beilstein Handbook Reference), SCHEMBL688787, 2,2,6,6-tetramethylpiperidone-4-toluene-p- sulfonate, CHEMBL117614, orb1301708, JWUXJYZVKZKLTJ-UHFFFAOYSA-, 2,6,6-Tetramethyl-4-piperidone, CHEBI:177813, HMS5083F16, 2,6,6-Tetramethyl-4-piperidinone, 2,2,6,6-teramethyl-4-piperidone, HY-N1131, NSC16579, STR06804, 2,2,6,6-Tetramethyl-g-piperidone, 2,6,6-Tetramethyl-4-oxopiperidine, Tox21_300816, 2,2,6,6-Tetramethyl-4 piperidone, CCG-44306, EBC-46160, SBB057185, STK256617, AKOS000120903, AC-2702, SB74533, 2,2,6, 6-Tetramethyl-4-piperidinone, NCGC00248182-01, NCGC00248182-02, NCGC00254720-01, CAS-826-36-8, DA-60001, piperidine, 2,2,6,6-tetramethyl-4-oxo-, 2,2,6,6-Tetramethyl-4-piperidone, 95%, TO0127900, CS-0016419, NS00008501, S4859, ST50307638, T1424, EN300-18105, P19976, AB00375601-03, F240897, Q6120732, SR-01000634150-1, F8889-5387, Z1250100692, InChI=1/C9H17NO/c1-8(2)5-7(11)6-9(3,4)10-8/h10H,5-6H2,1-4H3
Theoretical properties:
molecular_formula: C9H17NO
molecular_weight: 155.24 g/mol
exact_mass: 155.131014166 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 0
heavy_atom_count: 11
topological_polar_surface_area: 29.1 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 34.9 °C
Descriptions:
pubchem: Triacetonamine is a member of piperidones.
chembl: Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Triacetonamine is an organic compound with the formula OC(CH2CMe2)2NH (where Me = CH3).  It is a colorless or white solid that melts near room temperature.  The compound is an intermediate in the preparation of 2,2,6,6-tetramethylpiperidine, a sterically hindered base and precursor to the reagent called TEMPO.  Triacetonamine is formed by the poly-aldol condensation of acetone in the presence of ammonia and calcium chloride:

3 (CH3)2CO  +  NH3  →   OC(CH2CMe2)2NH  +  2 H2O
Reductive amination of triacetonamine gives 4-amino-2,2,6,6-tetramethylpiperidine.
It is primarily used as a stabilizer for plastics, typically via its conversion to number of hindered amine light stabilizers, but also finds use as a chemical feedstock. It is used to prepare the hindered amine 2,2,6,6-tetramethylpiperidine, CH2[CH2C(CH3)2]2NH, as well as the radical oxidizer 4-Hydroxy-TEMPO.
Triacetonamine has known application in the synthesis of alpha-eucaine. A surprising use of triacetonamine was in the synthesis of Elexacaftor.
A continuous process for the production of triacetonamine was developed: