Triethylamine → HCID 86640102, compound

HRID 555369Notes

Reaction equation

HRID 555369 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.[CH2:34]([N:36]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]1)[CH3:35]>CN(C=O)C>[CH2:34]([N:36]1[CH2:41][CH2:40][CH:39]([NH:42][CH2:2]/[C:3](/[CH2:15][O:16][C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)=[CH:4]/[C:5]2[CH:14]=[CH:13][C:8]([C:9]([O:11][CH3:12])=[O:10])=[CH:7][CH:6]=2)[CH2:38][CH2:37]1)[CH3:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 37349901-Ethylpiperidin-4-amineHCID 66987041HCID 66987041, compound

Product 1

HCID 86640102HCID 86640102, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl 4-[2-bromomethyl-3-(naphthalen-1-yloxy)-propenyl]-benzoate (412 mg, 1 mmol) was dissolved in N,N′-dimethylformamide (2.5 ml) in a 100 ml flask at 0° C., and to the resulting solution, triethylamine (0.17 ml, 1.2 mmol, 1.2 eq.) and 1-ethylpiperidin-4-ylamine (128 ml, 1.0 mmol, 1.0 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 mixture was concentrated under reduced pressure, 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 211 mg of the title compound as pale yellow oil (yield 46%).

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. concentrationthe mixture was concentrated under reduced pressure
  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-e19308aceeb141eeadd3c9dd8f912d6e
Source dataset
uspto-grants-2011_11
Patent number
US08053435B2

Reaction notes

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