Methanol → HCID 13907925, compound

HRID 652204Notes

Reaction equation

HRID 652204 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][N:5]([CH:17]1[CH2:22][C:21]([CH3:24])([CH3:23])[NH:20][C:19]([CH3:26])([CH3:25])[CH2:18]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[CH3:28][C:29]1([CH3:38])[CH2:34]C(O)[CH2:32][C:31]([CH3:37])([CH3:36])[NH:30]1.[NH2-].[Li+].CO>CCCCCCC>[CH3:28][C:29]1([CH3:38])[CH2:34][CH:1]([O:2][C:3](=[O:27])[CH2:4][N:5]([CH:17]2[CH2:22][C:21]([CH3:24])([CH3:23])[NH:20][C:19]([CH3:26])([CH3:25])[CH2:18]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:32][C:31]([CH3:37])([CH3:36])[NH:30]1

Participants

6

Reactant 4

HCID 887MethanolHCID 24532Lithium amideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 20199421HCID 20199421, compound

Product 1

HCID 13907925HCID 13907925, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

To the same flask as used in Example 1 were added 39.4 g (0.1 mole) of N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-undecanylglycine methyl ester, 17.3 g (0.11 mole) of 2,2,6,6-tetramethyl-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 32.1 g of N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-undecanylglycine(2,2,6,6-tetramethyl-4-piperidinyl)ester as a pale brown liquid. Yield, 61% based on N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-undecanylglycine methyl ester.

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-737e4ef07c4442ac8ed5114433259e0a
Source dataset
uspto-grants-1987_06
Patent number
US04670488

Reaction notes

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