1-Bromooctane → HCID 53936617, compound

HRID 1439960Notes

Reaction equation

HRID 1439960 reaction equation
[C:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([CH3:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1)(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=[O:5].Br[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(N(CC)CC)C.C([O-])([O-])=O.[K+].[K+]>CN(C)C(=O)C.O.C1(C)C=CC=CC=1>[C:4]([O:6][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])(=[O:5])[CH2:3][CH2:2][C:1]([O:8][CH:9]1[CH2:14][C:13]([CH3:15])([CH3:16])[N:12]([CH3:17])[C:11]([CH3:19])([CH3:18])[CH2:10]1)=[O:7]

Participants

8

Reactant 4

HCID 81401-BromooctaneHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 85850356HCID 85850356, compound

Product 1

HCID 53936617HCID 53936617, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 35.3 g (0.13 mol) of mono(1,2,2,6,6-pentamethyl-4-piperidyl) succinate, 25.1 g (0.13 mol) of 1-bromooctane and 13.2 g (0.13 mol) of triethylamine in 70 ml of anhydrous N,N-dimethylacetamide is heated for 4 hours at 85° C. After cooling to ambient temperature, 200 ml of water and 150 ml of toluene are added and a solution of 18 g (0.13 mol) of K2CO3 in 50 ml of water is then added slowly. After the end of the addition, the mixture is stirred for 15 minutes, the aqueous phase is separated off and the organic phase is washed with water until neutral and evaporated. The residue is distilled in vacuo. The product obtained has a boiling of 170° C./4 mbar.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. additionAfter the end of the addition
  3. customthe aqueous phase is separated off
  4. washthe organic phase is washed with water until neutral and
  5. customevaporated
  6. distillationThe residue is distilled in vacuo
  7. customThe product obtained
  8. customa boiling of 170° C./4 mbar

Sources & evidence

ORD record
ord-65f156421081438995d685012efbda26
Source dataset
uspto-grants-1996_03
Patent number
US05496875

Reaction notes

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