Sodium hydride → N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-3-(2-phenylethoxy)propanamine hydrochloride

HRID 863845Notes

Reaction equation

HRID 863845 reaction equation
I[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[ClH:14].[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]1[CH:34]=[CH:33][C:27]([CH2:28][O:29][CH2:30][CH2:31][NH2:32])=[CH:26][CH:25]=1.[H-].[Na+]>C1COCC1>[ClH:14].[O:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]1[CH:34]=[CH:33][C:27]([CH2:28][O:29][CH2:30][CH2:31][NH:32][CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 19420724(2-(3-Iodopropoxy)ethyl)benzeneHCID 194207502-[4-(Benzoxazol-2-yl)benzyloxy]ethylamine hydrochloride

Product 1

HCID 19420778N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-3-(2-phenylethoxy)propanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-iodo-3-(2-phenylethoxy)propane (0.566 g; 1.95 mmol) in dry THF (9 ml) is added 2-[4-(benzoxazol-2-yl)benzyloxy]ethylamine hydrochloride (0.59 g; 1.9 mmol). NaH (78 mg; 1.9 mmol) is then added at room temperature. The reaction mixture is heated at reflux for 30 minutes, then cooled, concentrated in vacuo, and the residue column chromatographed with 10% MeOH/CH2Cl2The product is dissolved in EtOH acidified with HCl/EtOH concentrated to a solid and recrystallized from CH2Cl2 /petroleum ether to obtain N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-3-(2-phenylethoxy)propanamine hydrochloride. (m.p. 134°-135° C.).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 30 minutes
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customthe residue column chromatographed with 10% MeOH/CH2Cl2The product
  6. dissolutionis dissolved in EtOH
  7. concentrationconcentrated to a solid
  8. customrecrystallized from CH2Cl2 /petroleum ether

Sources & evidence

ORD record
ord-4b25439a7ed848c4be21657385533479
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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