1-Aminopiperidine → HCID 21949047, compound

HRID 1025660Notes

Reaction equation

HRID 1025660 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13](O)=[O:14])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)[C:44]2[CH:45]=[CH:46][CH:47]=C[C:43]=2[N:42]=[N:41]1.NN1CCCCC1>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([NH:41][N:42]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]3)=[O:14])[N:10]=[C:9]2[C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 166581-AminopiperidineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21949064HCID 21949064, compound

Product 1

HCID 21949047HCID 21949047, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Part B: To a stirred suspension of 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-1H-imidazole-4-carboxylic acid (1.23 gram, 2.99 mmol) in dry acetonitrile (40 mL) is successively added diisopropylethylamine (DIPEA) (1.15 mL, 6.6 mmol), O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium hexafluorophos-phate (HBTU) (1.36 gram, 3.6 mmol) and 1-aminopiperidine (0.39 mL, 3.6 mmol). After stirring for 16 hours, the resulting mixture is concentrated in vacuo. The residue is dissolved in ethylacetate and an aqueous NaHCO3 solution is added. The ethylacetate layer is collected, washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. This solid is further purified by recrystallisation from acetonitrile to give 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-N-(piperidin-1-yl)-1H-imidazole-4-carboxamide (830 mg, 56% yield). Melting point: 219-221° C.

Workup

  1. concentrationthe resulting mixture is concentrated in vacuo
  2. dissolutionThe residue is dissolved in ethylacetate
  3. additionan aqueous NaHCO3 solution is added
  4. customThe ethylacetate layer is collected
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customto give a crude solid
  10. customThis solid is further purified by recrystallisation from acetonitrile

Sources & evidence

ORD record
ord-61217a0a03594c928a1bec7b25889397
Source dataset
uspto-grants-2014_05
Patent number
US08729101B2

Reaction notes

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