n-Butyl-2,2,6,6-tetramethyl-4-piperidinamine → Ethyl N-[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-1,3,5-triazin-6-yl]glycinate

HRID 375773Notes

Reaction equation

HRID 375773 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:3]=1.[CH3:16][C:17]1([CH3:30])[CH2:22][CH:21]([NH:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][C:19]([CH3:29])([CH3:28])[NH:18]1.C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1>[CH2:24]([N:23]([C:2]1[N:7]=[C:6]([N:23]([CH:21]2[CH2:22][C:17]([CH3:30])([CH3:16])[NH:18][C:19]([CH3:28])([CH3:29])[CH2:20]2)[CH2:24][CH2:25][CH2:26][CH3:27])[N:5]=[C:4]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:3]=1)[CH:21]1[CH2:20][C:19]([CH3:29])([CH3:28])[NH:18][C:17]([CH3:30])([CH3:16])[CH2:22]1)[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 118285n-Butyl-2,2,6,6-tetramethyl-4-piperidinamineHCID 516892Sodium BicarbonateHCID 147462614,6-dichloro-2-ethoxycarbonylmethylamino-S-triazine

Product 1

HCID 14746206Ethyl N-[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-1,3,5-triazin-6-yl]glycinateYield 96.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2.36 g of ethyl N-(2,4-dichloro-1,3,5-triazin-6-yl)glycinate [obtained as described in Preparation 4(A)], 4.19 g of 2,2,6,6-tetramethyl-4-(butylamino)piperidine [obtained as described in Preparation i(A)] and 2.77 g of sodium bicarbonate were heated under reflux in 20 ml of xylene for 29 hours. At the end of this time, the xylene was removed by distillation under reduced pressure, and a mixture of methylene chloride and water was added to the resulting residue, after which the mixture was shaken. The methylene chloride layer was separated, dried and concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (using a 20:10:1:1 by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent), to yield 5.46 g of the title compound melting at 40° C.

Workup

  1. customAt the end of this time, the xylene was removed by distillation under reduced pressure
  2. additiona mixture of methylene chloride and water
  3. additionwas added to the resulting residue
  4. customThe methylene chloride layer was separated
  5. customdried
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (
  8. additionby volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent),

Sources & evidence

ORD record
ord-4b2376a98a4048179b6e95cb7445ec51
Source dataset
uspto-grants-1996_01
Patent number
US05486556

Reaction notes

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