Methanol → HCID 13907926, compound

HRID 652205Notes

Reaction equation

HRID 652205 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][NH:5][CH:6]1[CH2:11][C:10]([CH3:13])([CH3:12])[N:9]([CH3:14])[C:8]([CH3:16])([CH3:15])[CH2:7]1.[CH3:18][N:19]1[C:24]([CH3:26])([CH3:25])[CH2:23]C(O)[CH2:21][C:20]1([CH3:29])[CH3:28].[NH2-].[Li+].CO>CCCCCCC>[CH3:18][N:19]1[C:24]([CH3:26])([CH3:25])[CH2:23][CH:1]([O:2][C:3](=[O:17])[CH2:4][NH:5][CH:6]2[CH2:7][C:8]([CH3:16])([CH3:15])[N:9]([CH3:14])[C:10]([CH3:13])([CH3:12])[CH2:11]2)[CH2:21][C:20]1([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 887MethanolHCID 24532Lithium amideHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-HCID 20199423HCID 20199423, compound

Product 1

HCID 13907926HCID 13907926, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

To the same flask as used in Example 1 were added 24.2 g (0.1 mole) of N-(1,2,2,6,6-pentamethyl-4-piperidinyl)glycine methyl ester, 18.7 g (0.11 mole) of 1,2,2,6,6-pentamethyl-4-piperidinol, 0.23 g of lithium amide and 100 g of heptane. The temperature was raised with stirring, and reaction was carried out at 98° to 105° C. for 6 hours, during which methanol was removed from the reaction system by means of the Deanstark trap. After completion of the reaction, water was added to the reaction solution to dissolve the product in the heptane layer. The heptane layer was separated, and heptane in the layer was removed by distillation to obtain 30 g of N-(1,2,2,6,6-pentamethyl-4-piperidinyl)glycine(1,2,2,6,6-pentamethyl-4-piperidinyl)ester as a pale yellow liquid. Yield, 79% based on N-(1,2,2,6,6-pentamethyl-4-piperidinyl)glycine methyl ester. A pale yellow oily product was obtained by the subsequent column chromatographic separation.

Workup

  1. temperatureThe temperature was raised
  2. customreaction
  3. customwas removed from the reaction system by means of the Deanstark trap
  4. customAfter completion of the reaction, water
  5. additionwas added to the reaction solution
  6. customThe heptane layer was separated
  7. customheptane in the layer was removed by distillation

Sources & evidence

ORD record
ord-2e9ff75cd6e34d63a73f5daeb31dbef2
Source dataset
uspto-grants-1987_06
Patent number
US04670488

Reaction notes

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