Sebacoyl chloride → Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate

HRID 2071929

Reaction equation

HRID 2071929 reaction equation
[CH3:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([OH:10])[CH2:4][C:3]1([CH3:12])[CH3:11].[C:13](Cl)(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23].Cl.[CH3:28][N:29]1[C:34]([CH3:36])([CH3:35])[CH2:33][CH:32]([OH:37])[CH2:31][C:30]1([CH3:39])[CH3:38]>C1C=CC=CC=1>[CH3:1][N:2]1[C:7]([CH3:8])([CH3:9])[CH2:6][CH:5]([O:10][C:13](=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:37][CH:32]2[CH2:31][C:30]([CH3:38])([CH3:39])[N:29]([CH3:28])[C:34]([CH3:36])([CH3:35])[CH2:33]2)=[O:23])[CH2:4][C:3]1([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 66072Sebacoyl chlorideHCID 754724-Piperidinol, 1,2,2,6,6-pentamethyl-HCID 204925221,2,2,6,6-Pentamethylpiperidin-4-ol hydrochloride

Product 1

HCID 586744Bis(1,2,2,6,6-pentamethyl-4-piperidyl) sebacate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 17.10 parts of 1,2,2,6,6-pentamethylpiperidin-4-ol in 50 parts of dry benzene was stirred at 15°-20° C. whilst adding 6.0 parts of sebacoyl chloride dropwise over 15 minutes. The mixture was stirred for a further 12 hours at room temperature after which the 1,2,2,6,6-pentamethylpiperidin-4-ol hydrochloride formed during the reaction was filtered off. The benzene was removed by distillation under reduced pressure to give a yellow oil, which was distilled under reduced pressure to give bis(1,2,2,6,6-pentamethyl-4-piperidinyl)sebacate as a colorless oil having a boiling point of 218°-20° C. at 0.4 mm of Hg and the following elemental analysis by weight:

Workup

  1. customformed during the reaction
  2. filtrationwas filtered off
  3. customThe benzene was removed by distillation under reduced pressure
  4. customto give a yellow oil, which
  5. distillationwas distilled under reduced pressure

Sources & evidence

ORD record
ord-d6a1f4ccd52d4c7ab93b0288f2581946
Source dataset
uspto-grants-1977_09
Patent number
US04049647

Linked notes

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