Sodium hydride → N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-6-phenyl-1-hexanamine hydrochloride

HRID 863841Notes

Reaction equation

HRID 863841 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]I)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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+].Cl.CCO>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][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 145296726-Phenyl-1-hexyl iodideHCID 194207502-[4-(Benzoxazol-2-yl)benzyloxy]ethylamine hydrochlorideHCID 21887872Ethanol hydrochloride

Product 1

HCID 19420773N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-6-phenyl-1-hexanamine hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-phenyl-1-hexyl iodide (0.63 g; 2.2 mmol) in THF (12 ml) is added 2-[4-(benzoxazol-2-yl)benzyloxy]ethylamine hydrochloride (0.6 g ; 2 mmol) followed by NaH (60% suspension; 0.11 g). The reaction mixture is stirred for 1 hour at room temperature and then heated for 1 1/2 hours at reflux. The mixture is next cooled, acidified with HCl/EtOH, concentrated and purified by column chromatography using 10% MeOH/CH2Cl2 as eluant. The resultant product is treated with HCl/EtOH and recrystallized from EtOH to give pure N-[2-(4-(benzoxazol-2-yl)benzyloxy)ethyl]-6-phenyl-1-hexanamine hydrochloride. (m.p. 163°-165° C.).

Workup

  1. temperatureheated for 1 1/2 hours
  2. temperatureat reflux
  3. concentrationconcentrated
  4. custompurified by column chromatography
  5. additionThe resultant product is treated with HCl/EtOH
  6. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-a5fcf69678a64981a41eed617b751558
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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