1-Phenethylamine → HCID 19019336, compound

HRID 2081670Notes

Reaction equation

HRID 2081670 reaction equation
[OH:1][CH2:2][C:3]1O[CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7](=[O:9])[CH:8]=1.[C:29]1([CH:35]([NH2:37])[CH3:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+].[K+].[Br-]>C(O)C.O>[OH:1][CH2:2][C:3]1[N:37]([CH:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:36])[CH:5]=[C:6]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[C:7](=[O:9])[CH:8]=1

Participants

7

Reactant 4

HCID 74081-PhenethylamineHCID 10340Sodium CarbonateHCID 253877Potassium BromideHCID 14749912HCID 14749912, compound

Product 1

HCID 19019336HCID 19019336, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 8.0 g (0.02 Mol) 2-hydroxymethyl-5-octadecyloxy-4-pyranone, 4.8 g (0.04 Mol) (±)-1-phenylethylamine, 1.5 g Na2CO3, 10 mL water and 100 mL ethanol is boiled under reflux for 72 hours. After cooling the solvent and the excess of amine is removed under vacuum and the residue is mixed with water and extracted with dichloromethane. The organic phase is dried over Na2SO4, evaporated and the obtained resin is purified by column chromatography on silica gel with dichloromethane with 1-2% methanol to give a yellow oil, which is changing to wax-like consistency. IR (KBr): 1630 (C=O), MS (m/l) 497 (M+).

Workup

  1. temperatureunder reflux for 72 hours
  2. temperatureAfter cooling the solvent
  3. customthe excess of amine is removed under vacuum
  4. additionthe residue is mixed with water
  5. extractionextracted with dichloromethane
  6. dry with materialThe organic phase is dried over Na2SO4
  7. customevaporated
  8. customthe obtained resin is purified by column chromatography on silica gel with dichloromethane with 1-2% methanol
  9. customto give a yellow oil, which

Sources & evidence

ORD record
ord-0c928793d40748728008281ed544a38e
Source dataset
uspto-grants-1993_02
Patent number
US05185352

Reaction notes

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