Hydrochloric Acid → (4,5-Dihydro-oxazol-2-yl)-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine

HRID 1633712Notes

Reaction equation

HRID 1633712 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][NH:22][CH3:23])=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)=[CH:4][CH:3]=1.Cl[CH2:25][CH2:26][N:27]=[C:28]=[O:29].CCN(CC)CC.Cl>C1COCC1>[O:29]1[CH2:25][CH2:26][N:27]=[C:28]1[N:22]([CH2:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[CH:12]=[C:11]2[C:16](=[CH:15][CH:14]=1)[N:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[CH:9]=[CH:10]2)[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 160352-Chloroethyl isocyanateHCID 18679487{4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine

Product 1

HCID 18679437(4,5-Dihydro-oxazol-2-yl)-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amineYield 16.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

300 mg (0.96 mmol) {4-[1-(4-Fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methylamine in 10 ml THF were treated with 150 mg (1.4 mmol) 2-chloroethylisocyanate and the mixture stirred at room temperature during 10 hours. After addition of 0.2 ml NEt3 the mixture was stirred for an additional hour and treated with 0.1 M aqueous HCl. Extraction with Et2O, drying of the combined organic layers with Na2SO4, Evaporation of the solvent, and column chromatography on silica gel with CH2Cl2/MeOH/NEt3 10:1:0.1 gave 60 mg (16%) (4,5-Dihydro-oxazol-2-yl)-{4-[1-(4-fluoro-phenyl)-1H-indol-5-yloxy]-butyl}-methyl-amine, MS: 382 (MH+).

Workup

  1. stirringwas stirred for an additional hour
  2. extractionExtraction with Et2O
  3. dry with materialdrying of the combined organic layers with Na2SO4, Evaporation of the solvent, and column chromatography on silica gel with CH2Cl2/MeOH/NEt3 10:1:0.1

Sources & evidence

ORD record
ord-534d6daf4726461fa0e9c57a7f25f3f1
Source dataset
uspto-grants-2003_01
Patent number
US06503907B2

Reaction notes

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