Methanol → HCID 13907924, compound

HRID 652202Notes

Reaction equation

HRID 652202 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]([CH:10]1[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]1)[CH2:6][CH2:7][CH2:8][CH3:9].[CH3:21][C:22]1([CH3:31])[CH2:27]C(O)[CH2:25][C:24]([CH3:30])([CH3:29])[NH:23]1.[NH2-].[Li+].CO>CCCCCCCC>[CH3:21][C:22]1([CH3:31])[CH2:27][CH:1]([O:2][C:3](=[O:20])[CH2:4][N:5]([CH:10]2[CH2:15][C:14]([CH3:17])([CH3:16])[NH:13][C:12]([CH3:19])([CH3:18])[CH2:11]2)[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:25][C:24]([CH3:30])([CH3:29])[NH:23]1

Participants

6

Reactant 4

HCID 887MethanolHCID 24532Lithium amideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 20199426HCID 20199426, compound

Product 1

HCID 13907924HCID 13907924, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 356OctaneSolvent2×

Procedure

To the same flask as used in Example 1 were added 28.4 g (0.1 mole) of N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-n-butylglycine methyl ester, 17.3 g (0.11 mole) of 2,2,6,6-tetramethyl-4-piperidinol, 0.23 g (0.01 mole) of lithium amide and 100 g of n-octane. The temperature was raised with stirring, and reaction was carried out at 128° to 130° C. for 5 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 n-octane. The n-octane layer was separated, and n-octane in the layer was removed by distillation to obtain 33.1 g of N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-n-butylglycine(2,2,6,6-tetramethyl-4-piperidinyl)ester as a brown oily product. Yield, 81% based on N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-n-butylglycine 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 n-octane layer was separated
  7. customn-octane in the layer was removed by distillation

Sources & evidence

ORD record
ord-bfba15378e7a490db0a592eb83ef83f5
Source dataset
uspto-grants-1987_06
Patent number
US04670488

Reaction notes

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