Triethylamine → HCID 66671479, compound

HRID 446499Notes

Reaction equation

HRID 446499 reaction equation
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:20])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][NH:18][CH3:19])[CH2:12][CH2:11]1.[CH2:27]([N:29](CC)CC)C.Br[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](Cl)=[O:41].CN.CO>C(Cl)Cl.O>[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:20])[O:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][N:18]([CH3:19])[C:40](=[O:41])[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][NH:29][CH3:27])[CH2:12][CH2:11]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 898486-Bromohexanoyl chlorideHCID 566436031-(2-(Methylamino)ethyl)piperidin-4-yl [1,1'-biphenyl]-2-ylcarbamateHCID 57454252Monomethylamine methanol

Product 1

HCID 66671479HCID 66671479, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-[2-(Methylamino)ethyl]piperidin-4-yl biphenyl-2-ylcarbamate (500 mg, 1.41 mmol) was dissolved in methylene chloride (5 mL), triethylamine (0.236 mL, 1.70 mmol) and 6-bromohexanoyl chloride (0.232 mL, 1.56 mmol) were added under ice cooling, and the mixture was stirred at room temperature for 30 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate (×3) and washed with saturated sodium chloride solution. The organic layer was dried with anhydrous sodium sulfate, then the solvent was evaporated under reduced pressure, the resulting residue was dissolved in methylene chloride (5 mL), a 40% methyl amine-methanol solution (5.76 mL, 56.4 mmol) was added under ice cooling, and the mixture was stirred at room temperature for 7.5 hours. The solvent of the reaction mixture was evaporated under reduced pressure, and the resulting residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=100:0→10:1, v/v) to give the title compound (574 mg; yield, 85%) as a light yellow oily substance.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (×3)
  2. washwashed with saturated sodium chloride solution
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionthe resulting residue was dissolved in methylene chloride (5 mL)
  6. stirringthe mixture was stirred at room temperature for 7.5 hours
  7. customThe solvent of the reaction mixture was evaporated under reduced pressure
  8. customthe resulting residue was purified by NH silica gel column chromatography (ethyl acetate

Sources & evidence

ORD record
ord-37235c7c31df4f0292ec89dcf6de5b3f
Source dataset
uspto-grants-2013_07
Patent number
US08476253B2

Reaction notes

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