Carbon Dioxide → HCID 23295933, compound

HRID 361510Notes

Reaction equation

HRID 361510 reaction equation
[OH:1][CH:2]([CH2:19]O)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18].[BrH:21].[C:22]([OH:25])(=O)[CH3:23].C(=O)(O)[O-].[Na+].C(=O)=O>ClCCl>[C:22]([O:1][CH:2]([CH2:19][Br:21])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=[O:18])(=[O:25])[CH3:23]

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 516892Sodium BicarbonateHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 23287953HCID 23287953, compound

Product 1

HCID 23295933HCID 23295933, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To N-(10,11-dihydroxyundecyl)-2-piperidone (4.21 g, 14.8 mmol) was added 30% hydrogen bromide-acetic acid (8.7 mL) and the mixture was then stirred for 1 hour. The solution was poured carefully into a mixture of sodium bicarbonate (15 g), ice water (150 mL), and dichloromethane (100 mL). After carbon dioxide evolution has subsided, the organic layer was separated and the aqueous layer extracted with dichloromethane (2×80ML). The combined organic layers was dried over sodium sulfate and the solvent evaporated under vacuum to give 1-(10-acetoxy-11-bromoundecyl)-2-piperidone (4.9 g, 89% yield) as a viscous oil which dissolves in methanol (10 mL). A 1M sodium methoxide (15 mL, 15 mmol) in methanol solution was added all at once. After stirring for 1 hour, the solution was treated with water (50 mL) and then extracted with dichloromethane (3×50 mL). The combined extracts were dried over sodium sulfate and the solvent evaporated under vacuum. The residue was purified by chromatography using ethyl acetate to yield 2.40 g (61% yield) N-(10,11-Oxidoundecyl)-2-piperidone as a colorless oil.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer extracted with dichloromethane (2×80ML)
  3. dry with materialThe combined organic layers was dried over sodium sulfate
  4. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-a0f2b99e0c24467aa509f9c68f4d0569
Source dataset
uspto-grants-1999_02
Patent number
US05866576

Reaction notes

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