Ethylenediamine → 4-(2-Aminoethyl)-1-(4-trifluoromethylpyrimidin-2-yl)-piperidin-4-ol

HRID 1019707Notes

Reaction equation

HRID 1019707 reaction equation
ClC1C(Cl)=C(Cl)C(Cl)=C2C=1C(=O)[N:5]([CH2:15][CH2:16][C:17]1([OH:33])[CH2:22][CH2:21][N:20]([C:23]3[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=3)[CH2:19][CH2:18]1)C2=O.C(N)CN>C(#N)C.O1CCCC1.O.C(O)C>[NH2:5][CH2:15][CH2:16][C:17]1([OH:33])[CH2:18][CH2:19][N:20]([C:23]2[N:28]=[C:27]([C:29]([F:31])([F:32])[F:30])[CH:26]=[CH:25][N:24]=2)[CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 866613504,5,6,7-Tetrachloro-2-{2-[4-hydroxy-1-(4-trifluoromethylpyrimidin-2-yl)piperidin-4-yl]ethyl}isoindole-1,3-dione

Product 1

HCID 666606194-(2-Aminoethyl)-1-(4-trifluoromethylpyrimidin-2-yl)-piperidin-4-olYield 76%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 18694733Acetonitrile tetrahydrofuran waterSolvent

Procedure

The process is performed according to the procedure described in Example 1 (step 1.4.). Starting with 0.38 g (0.68 mmol) of 4,5,6,7-tetrachloro-2-{2-[4-hydroxy-1-(4-trifluoromethylpyrimidin-2-yl)piperidin-4-yl]ethyl}isoindole-1,3-dione), obtained in the preceding step, dissolved in an acetonitrile/tetrahydrofuran/water mixture (2/1/1) and 0.18 g (3.06 mmol) of ethylenediamine in 4.50 mL of ethanol, and after chromatography on silica gel, eluting with a 90/10/1 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.15 g of expected product is obtained in the form of a wax.

Workup

  1. customobtained in the preceding step
  2. washafter chromatography on silica gel, eluting with a 90/10/1 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record
ord-da33538208e64ece8c9558910da8f5cf
Source dataset
uspto-grants-2014_05
Patent number
US08716289B2

Reaction notes

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