3-Iodoaniline → HCID 19081605, compound

HRID 963417Notes

Reaction equation

HRID 963417 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[O:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1.[BH4-].[Na+]>C1(C)C=CC=CC=1.O.CO>[I:1][C:2]1[CH:3]=[C:4]([NH:5][CH:12]2[CH2:13][CH2:14][O:9][CH2:10][CH2:11]2)[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 3

HCID 122713-IodoanilineHCID 121599Tetrahydro-4H-pyran-4-oneHCID 4311764Sodium borohydride

Product 1

HCID 19081605HCID 19081605, compoundYield 20%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Procedure

13bd) A mixture of 2 g of 3-iodoaniline and 1.26 ml of tetrahydro-4H-pyran-4-one is boiled in 50 ml of toluene on a water separator for 4 hrs. The solution of the imine which remains behind is treated with 20 ml of methanol and 520 mg of sodium borohydride are added in portions. The mixture is stirred at room temperature for 16 hrs., then poured into water and extracted with ethyl acetate. Chromatography on silica gel with ethyl acetate/hexane 3:7 gives 559 mg of (3-iodo-phenyl)-(tetrahydropyran-4-yl)-amine as a colourless oil. Yield: 20%. Mass spectrum: peaks inter alia at m/e: 303 (M+, 100%), 245 (40%), 219 (40%), 130 (90%), 117 (62%).

Workup

  1. additionare added in portions
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-efb485bb25b64e1d8e752674478a85e3
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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