Triethylamine → HCID 86661264, compound

HRID 2408214Notes

Reaction equation

HRID 2408214 reaction equation
[CH2:1]([NH2:11])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C(N(CC)CC)C.[C:19]([O:22][CH:23]([CH3:27])[C:24](Cl)=[O:25])(=[O:21])[CH3:20]>C1COCC1.ClCCl>[CH2:1]([NH:11][C:24](=[O:25])[CH:23]([O:22][C:19](=[O:21])[CH3:20])[CH3:27])/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 45474922-Acetoxypropionyl ChlorideHCID 5475462Geranylamine

Product 1

HCID 86661264HCID 86661264, compoundYield 103.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a cold solution of geranyl amine (7 g) and triethyl amine (6 g) in THF (50 ml) was added dropwise a solution of 2-acetoxypropanoyl chloride (9 g) in dichloromethane (15 ml) at a temperature between 6° C. and 13° C. over a period of 20 minutes. Stirring was continued at room temperature for 2 hrs. The white precipitate (triethylamine HCl salt) was filtered and the filtrate was evaporated. The residue was dissolved in DCM (100 ml), washed twice with 50 ml of aqueous 5% HCl solution and twice with water (2×50 ml) and evaporated to dryness to yield 12.6 g of a colourless oil. The yield was 90%, the purity was 95% according to NMR analysis.

Workup

  1. filtrationThe white precipitate (triethylamine HCl salt) was filtered
  2. customthe filtrate was evaporated
  3. dissolutionThe residue was dissolved in DCM (100 ml)
  4. washwashed twice with 50 ml of aqueous 5% HCl solution and twice with water (2×50 ml)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-03d43af80eab49478477b31fcbe7d389
Source dataset
uspto-grants-2014_08
Patent number
US08815321B2

Reaction notes

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