Phenethylamine → HCID 58109350, compound

HRID 2037474Notes

Reaction equation

HRID 2037474 reaction equation
Cl[CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7].[CH2:15]([NH2:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:15]([NH:23][CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 159334751-Chloro-3-phenylhex-5-en-3-ol

Product 1

HCID 58109350HCID 58109350, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-chloro-3-phenyl-hex-5-en-3-ol (500 mg, 2.38 mmol), phenethylamine (348 mg, 2.862.24 mmol), and K2CO3 (643 mg, 4.76 mmol) in anhydrous CH3CN (10 mL) were stirred at rt under N2. Then the solution was refluxing at 80-90° C. overnight. The solid was filtered, and the filtrate was condensed under reduced pressure to give the residue, which was purified by preparative TLC to afford 1-phenethylamino-3-phenyl-hex-5-en-3-ol (320 mg, 45%). 1H NMR (CDCl3): 2.07-2.15 (m, 1H), 2.28-2.39 (m, 1H), 2.51-2.69 (m, 3H), 2.81 (m, 1H), 2.90-3.01 (m, 3H), 3.09 (m, 1H), 5.04 (m, 2H), 5.47-5.58 (m, 1H), 7.17-7.38 (m, 11H).

Workup

  1. temperatureThen the solution was refluxing at 80-90° C. overnight
  2. filtrationThe solid was filtered
  3. customcondensed under reduced pressure
  4. customto give the residue, which
  5. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-df7cb22dadd9442eac9e3217e028c8d6
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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