Piperidine → HCID 22475117, compound

HRID 2103125Notes

Reaction equation

HRID 2103125 reaction equation
[Li+].[CH3:2][C:3]1[C:4]([C:24]([O-])=[O:25])=[CH:5][C:6]2[O:10][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[O:8][C:7]=2[CH:23]=1.C[N+](C)=C(N(C)C)O[N:31]1[C:35]2C=[CH:37][CH:38]=[CH:39][C:34]=2N=N1.F[P-](F)(F)(F)(F)F.N1CCCCC1>CN(C)C=O>[CH3:2][C:3]1[C:4]([C:24]([N:31]2[CH2:37][CH2:38][CH2:39][CH2:34][CH2:35]2)=[O:25])=[CH:5][C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[O:8][C:7]=2[CH:23]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 69059954HCID 69059954, compound

Product 1

HCID 22475117HCID 22475117, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 6-methyl-2,2-diphenyl-1,3-benzodioxole-5-carboxylic acid lithium salt (101.5 mg, 0.3 mmol) in N,N-dimethylformamide (3 mL) was added N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)-uronium-hexafluorophosphate (114 mg, 0.3 mmol, 1.0 eq.). The reaction mixture was stirred 1 h at 20° C. Piperidine (26 mg, 0.3 mmol, 1.0 eq.) was added and the reaction mixture was stirred 20 h at 20° C. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water, brine and then dried over sodium sulfate, filtered and evaporated. Purification by flash chromatography afforded the title compound (73 mg, 61%) as a light yellow solid.

Workup

  1. stirringthe reaction mixture was stirred 20 h at 20° C
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washThe combined organic layer was washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by flash chromatography

Sources & evidence

ORD record
ord-648c34780f9244ae9d95eea19e9edc6b
Source dataset
uspto-grants-2009_08
Patent number
US07576088B2

Reaction notes

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