Piperidine → HCID 10108875, compound

HRID 1826829Notes

Reaction equation

HRID 1826829 reaction equation
[C:1]1([C:7]2[N:11]3[CH:12]=[C:13]([C:20]([OH:22])=O)[C:14]4[C:19]([C:10]3=[CH:9][N:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.[N:30]1(O[P+](N(C)C)(N(C)C)N(C)C)[C:34]2C=[CH:36][CH:37]=[CH:38][C:33]=2N=N1.N1CCCCC1.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:1]1([C:7]2[N:11]3[CH:12]=[C:13]([C:20]([N:30]4[CH2:36][CH2:37][CH2:38][CH2:33][CH2:34]4)=[O:22])[C:14]4[C:19]([C:10]3=[CH:9][N:8]=2)=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 516892Sodium BicarbonateHCID 22136183HCID 22136183, compound

Product 1

HCID 10108875HCID 10108875, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from part 9 (95 mg), BOP (220 mg), piperidine (56 mg) and TEA (67 mg) in 2 ml of DMF is stirred at room temperature for 18 hours. The mixture is added to aqueous NaHCO3 solution and extracted with EtOAc. The organic layer is washed with brine and water, dried (Na2SO4), filtered and concentrated to afford a foam. Purification on a silica gel column, eluting with 5% methanol in methylene chloride, gives the title compound. 1H NMR (CDCl3) δ 1.38–1.50 and 1.60–1.80 (6H, m), 3.18–3.36 (2H, m), 3.65–3.95 (2H, m), 7.40–7.60 (6H, m), 7.75 (2H, d), 7.95 (1H, s), 8.05 (1H, s), 8.10 (1H, d). The hydrochloride salt was prepared by treating the free base in EtOAc with a solution of hydrogen chloride in ether and collecting by filtration.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer is washed with brine and water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford a foam
  7. customPurification on a silica gel column
  8. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-8b113284f78340d89c65c87ccc7ca0a5
Source dataset
uspto-grants-2006_05
Patent number
US07053093B2

Reaction notes

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