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Methanol → HCID 20199417, compound

HRID 652203
Notes
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Reaction equation

HRID 652203 reaction equation
[CH3:1][O:2][C:3](=[O:24])[CH2:4][N:5]([CH:14]1[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH3:25][C:26]1([CH3:35])[CH2:31]C(O)[CH2:29][C:28]([CH3:34])([CH3:33])[NH:27]1.CC(C)([O-])C.[K+].CO>CCCCCCC>[CH3:25][C:26]1([CH3:35])[CH2:31][CH:1]([O:2][C:3](=[O:24])[CH2:4][N:5]([CH:14]2[CH2:19][C:18]([CH3:21])([CH3:20])[NH:17][C:16]([CH3:23])([CH3:22])[CH2:15]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[CH2:29][C:28]([CH3:34])([CH3:33])[NH:27]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 754714-Hydroxy-2,2,6,6-tetramethylpiperidineHCID 20199414HCID 20199414, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 20199417HCID 20199417, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 8900
Heptane
Solvent
2×

Procedure

To the same flask as used in Example 1 were added 34 g (0.1 mole) of N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-octylglycine methyl ester, 17.3 g (0.11 mole) of 2,2,6,6-tetramethyl-4-piperidinol, 1.2 g of potassium tert-butoxide 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 34.3 g of N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-octylglycine(2,2,6,6-tetramethyl-4-piperidinyl)ester as a pale brown oily product. Yield, 74% based on N-(2,2,6,6-tetramethyl-4-piperidinyl)-N-octylglycine 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-1bdbf90ffdfa4f9a9d91532a02c73e94
Source dataset
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04670488

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes