Piperidine → HCID 69047415, compound

HRID 733176Notes

Reaction equation

HRID 733176 reaction equation
O[C:2](=[O:23])[CH2:3][CH2:4][C:5]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[N:8]=[C:7]([C:21]#[N:22])[N:6]=1.O[N:25]1[C:29]2C=[CH:31][CH:32]=[CH:33][C:28]=2N=N1.Cl.CN(C)CCCN=C=NCC.N1CCCCC1>C(Cl)Cl>[N:25]1([C:2](=[O:23])[CH2:3][CH2:4][C:5]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=3)[N:8]=[C:7]([C:21]#[N:22])[N:6]=2)[CH2:31][CH2:32][CH2:33][CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 52949411HCID 52949411, compound

Product 1

HCID 69047415HCID 69047415, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3-hydroxy-3-oxopropyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile (64 mg) in DCM (6 mL) was added 1-hydroxybenzotriazole (30 mg) and 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide HCl (38 mg). The solution was stirred at room temperature for 15 min and piperidine (22 mg) added. After standing for 18 h, the reaction mixture was washed with HCl (1M, 2×5 ml), H2O then brine and dried with sodium sulfate. After removal of solvent, crystallisation from a trace of acetone/ether gave 4-(3-piperidin-1-yl-3-oxopropyl)-6-(3-trifluoromethylphenyl)-pyrimidine-2-carbonitrile as a white solid, 35 mg.

Workup

  1. waitAfter standing for 18 h
  2. washthe reaction mixture was washed with HCl (1M, 2×5 ml), H2O
  3. dry with materialbrine and dried with sodium sulfate
  4. customAfter removal of solvent, crystallisation from a trace of acetone/ether

Sources & evidence

ORD record
ord-05e52e0541a4413581b3266c290131ee
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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