Ethyl formate → N-Cyclohexyl-N-(2,2,6,6-tetramethyl-4-piperidinyl)formamide

HRID 1110689Notes

Reaction equation

HRID 1110689 reaction equation
[CH:1]1([NH:7][CH:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:18](OCC)=[O:19]>CCCCO.CCCCO.CCCCO.CCCCO.[Ti]>[CH:1]1([N:7]([CH:8]2[CH2:13][C:12]([CH3:15])([CH3:14])[NH:11][C:10]([CH3:17])([CH3:16])[CH2:9]2)[CH:18]=[O:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 729174ST038767

Product 1

HCID 14419060N-Cyclohexyl-N-(2,2,6,6-tetramethyl-4-piperidinyl)formamide

Reagents, catalysts & solvents 1

HCID 521701TetrabutoxytitaniumCatalyst

Procedure

80 g of 4-(N-cyclohexylamino)-2,2,6,6-tetramethylpiperidine and 32 g of tetrabutyl orthotitanate in 175 ml of ethyl formate were refluxed for 11 hours. Fractional distillation gave a fraction of boiling point 143°-144° C. under 0.4 mmHg. After solidification, this fraction was recrystallized from n-hexane. 4-(N-cyclohexyl-N-formylamino)-2,2,6,6-tetramethylpiperidine was isolated as a colorless solid of melting point 105° C.

Workup

  1. distillationFractional distillation
  2. customgave a fraction of boiling point 143°-144° C. under 0.4 mmHg
  3. customAfter solidification, this fraction was recrystallized from n-hexane

Sources & evidence

ORD record
ord-5b7b836826304f49898d9f28caa364e8
Source dataset
uspto-grants-1990_12
Patent number
US04976889

Reaction notes

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