Methanol → HCID 20199427, compound

HRID 652206Notes

Reaction equation

HRID 652206 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH:4]([NH:6][CH:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[NH:10][C:9]([CH3:16])([CH3:15])[CH2:8]1)[CH3:5].[CH3:18][C:19]1([CH3:28])[CH2:24]C(O)[CH2:22][C:21]([CH3:27])([CH3:26])[NH:20]1.[NH2-].[Li+].CO>CCCCCCC>[CH3:18][C:19]1([CH3:28])[CH2:24][CH:1]([O:2][C:3](=[O:17])[CH:4]([NH:6][CH:7]2[CH2:8][C:9]([CH3:16])([CH3:15])[NH:10][C:11]([CH3:14])([CH3:13])[CH2:12]2)[CH3:5])[CH2:22][C:21]([CH3:27])([CH3:26])[NH:20]1

Participants

6

Reactant 4

HCID 887MethanolHCID 24532Lithium amideHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 66173697HCID 66173697, compound

Product 1

HCID 20199427HCID 20199427, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent2×

Procedure

To the same flask as used in Example 1 were added 24.4 g (0.1 mole) of N-(2,2,6,6-tetramethyl-4-piperidinyl)aminopropionic acid 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 28 g of N-(2,2,6,6-tetramethyl-4-piperidinyl)aminopropionic acid (2,2,6,6-tetramethyl-4-piperidinyl)ester as a pale yellow liquid. Yield, 73.5% based on N-(2,2,6,6-tetramethyl-4-piperidinyl)aminopropionic acid 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-4b3ebeed43024bb683c9f8fab65a85e2
Source dataset
uspto-grants-1987_06
Patent number
US04670488

Reaction notes

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