Piperidine → HCID 22104550, compound

HRID 1457320Notes

Reaction equation

HRID 1457320 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][CH2:13][C:14]([OH:16])=O.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>ClCCl>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][CH2:13][C:14]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 3268016HCID 3268016, compound

Product 1

HCID 22104550HCID 22104550, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,2,3,4-tetrahydro-1-oxo-2-naphthalenepropanoic acid (6.3 g), piperidine (3.7 g) and BOP Reagent (15.4 g) in dichloromethane (150 ml) was added dropwise triethylamine (3.5 g) at 25° C., and the mixture was refluxed for three hours. The reaction mixture was washed successively with water and 10% hydrochloric acid, and dried over anhydrous magnesium sulfate. The resultant was concentrated under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate=10:1), and the fractions containing the desired compound were combined, and concentrated under reduced pressure to give the desired compound (7.1 g) as an oily product.

Workup

  1. temperaturethe mixture was refluxed for three hours
  2. washThe reaction mixture was washed successively with water and 10% hydrochloric acid
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationThe resultant was concentrated under reduced pressure
  5. customto remove the solvent
  6. customthe residue was purified by silica gel column chromatography (eluent; toluene:ethyl acetate=10:1)
  7. additionthe fractions containing the desired compound
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-27ee4a547fd8450b8be9d835c6092b7b
Source dataset
uspto-grants-1998_12
Patent number
US05847159

Reaction notes

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