Triethylamine → HCID 86640103, compound

HRID 555370Notes

Reaction equation

HRID 555370 reaction equation
Br[CH2:2][C:3]([CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=[CH:4][C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:34][N:35]1[CH2:39][CH2:38][CH2:37][CH:36]1[CH2:40][CH2:41][NH2:42]>C(#N)C>[CH3:34][N:35]1[CH2:39][CH2:38][CH2:37][CH:36]1[CH2:40][CH2:41][NH:42][CH2:2]/[C:3](/[CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=[CH:4]/[C:5]1[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 983882-(2-Aminoethyl)-1-methylpyrrolidineHCID 66987041Methyl 4-[2-bromomethyl-3-(naphthalen-1-yloxy)-propenyl]-benzoate

Product 1

HCID 86640103HCID 86640103, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4-[2-bromomethyl-3-(naphthalen-1-yloxy)-propenyl]-benzoate (412 mg, 1 mmol) was dissolved acetonitrile (5 ml) in a 100 ml vessel at 0° C., and thereto triethylamine (0.21 ml, 1.5 mmol, 1.5 eq.) and 2-(1-methylpyrrolidin-2-yl)ethylamine (R1′″NH2; 0.22 ml, 1.5 mmol, 1.5 eq.) were added while stirring. The resulting mixture was heated from 0° C. to room temperature, and then reacted for 4 hours. After the completion of reaction, the solvent was distilled off, and the residue thus obtained was extracted with ethyl ester. The organic layer was separated, washed with an aqueous saturated sodium bicarbonate solution and brine in order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography to obtain 220 mg of the title compound as pale yellow oil (yield 48%).

Workup

  1. temperatureThe resulting mixture was heated from 0° C. to room temperature
  2. customreacted for 4 hours
  3. customAfter the completion of reaction
  4. distillationthe solvent was distilled off
  5. customthe residue thus obtained
  6. extractionwas extracted with ethyl ester
  7. customThe organic layer was separated
  8. washwashed with an aqueous saturated sodium bicarbonate solution and brine in order
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. customThe residue thus obtained

Sources & evidence

ORD record
ord-3ff10d82e5484b3c9ff5fa6c7a4e81f2
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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