Phenethylamine → HCID 14855251, compound

HRID 330406Notes

Reaction equation

HRID 330406 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:12]([NH2:20])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.C(Cl)[Cl:29]>C(O)C.CCOCC>[ClH:29].[O:1]([CH2:8][CH2:9][CH2:10][NH:20][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 6344DichloromethaneHCID 8471TriethylamineHCID 68522Benzene, (3-bromopropoxy)-

Product 1

HCID 14855251HCID 14855251, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 30 g (0.14 mole) of 3-phenoxypropyl bromide and 16.82 g (0.139 mole) of phenethylamine in 500 ml of absolute ethanol and in the presence of excess triethylamine was refluxed for 18 hr. The solvent was removed in vacuo and the residue was partitioned between methylene chloride and dilute sodium hydroxide. The methylene chloride solution was dried over magnesium sulfate, and the solvent was removed in vacuo to give an oil. This was dissolved in a mixture of ether and methylene chloride, and the solution was extracted with dilute sulfuric acid and then with dilute sodium hydroxide. The organic solution was treated with an excess of ethereal hydrogen chloride, and 12.43 g (30.68%) of the product precipitated as a white, crystalline solid, mp 196°-197° C.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between methylene chloride and dilute sodium hydroxide
  3. dry with materialThe methylene chloride solution was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customto give an oil
  6. extractionthe solution was extracted with dilute sulfuric acid
  7. additionThe organic solution was treated with an excess of ethereal hydrogen chloride, and 12.43 g (30.68%) of the product
  8. customprecipitated as a white, crystalline solid, mp 196°-197° C.

Sources & evidence

ORD record
ord-55bd62b05e3a435794fe06a21d83169f
Source dataset
uspto-grants-1990_01
Patent number
US04895840

Reaction notes

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