4-Amino-2,2,6,6-tetramethylpiperidine → HCID 67358775, compound

HRID 1668840Notes

Reaction equation

HRID 1668840 reaction equation
Cl[C:2]1[C:18]2[C:6](=[C:7]([CH3:21])[C:8]3[NH:9][C:10]4[CH:11]=[CH:12][C:13]([O:19][CH3:20])=[CH:14][C:15]=4[C:16]=3[CH:17]=2)[CH:5]=[CH:4][N:3]=1.[NH2:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[NH:26][C:25]([CH3:32])([CH3:31])[CH2:24]1>>[CH3:20][O:19][C:13]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[C:7]([CH3:21])=[C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:22][CH:23]5[CH2:24][C:25]([CH3:32])([CH3:31])[NH:26][C:27]([CH3:30])([CH3:29])[CH2:28]5)[C:18]4=[CH:17][C:16]=3[C:15]=2[CH:14]=1

Participants

3

Reactant 2

HCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 178488042HCID 178488042, compound

Product 1

HCID 67358775HCID 67358775, compoundYield 71%

Conditions

Temperature
150 °C

Procedure

The mixture of 1-chloro-9-methoxy-5-methyl-6H-pyrido[4,3-b]carbazole (1.0 g; product known, already published) and 4-amino-2,2,6,6-tetramethylpiperidin (1.0 g) is heated at 150° C. for 21 h. Excess amino is eliminated by evaporation under reduced pressure. Water is added to the residue obtained to form a solid. This solid is filtered, washed with water, then recrystallized from xylene to yield the expected (9-methoxy-5-methyl-6H-pyrido[4,3-b]carbazol-1-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (1.0 g, 71% yield) in the form of yellow microcrystals (melting point: 223-225° C.). NMR in agreement.

Workup

  1. customExcess amino is eliminated by evaporation under reduced pressure
  2. additionWater is added to the residue
  3. customobtained
  4. customto form a solid
  5. filtrationThis solid is filtered
  6. washwashed with water
  7. customrecrystallized from xylene

Sources & evidence

ORD record
ord-a56b4db269e543549c738b2c76b0889e
Source dataset
uspto-grants-2011_08
Patent number
US07989467B2

Reaction notes

Loading…