Piperidine → HCID 21939982, compound

HRID 1242890Notes

Reaction equation

HRID 1242890 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][C:14]([OH:16])=O)[CH2:7][CH2:6]2.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1.C(#N)C.C(OCC)(=O)C.O.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([CH2:13][C:14]([N:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:16])[CH2:7][CH2:6]2

Participants

10

Reactant 4

HCID 8082PiperidineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 21939949(6-Methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)acetic acid

Product 1

HCID 21939982HCID 21939982, compoundYield 89.7%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(6-Methoxy-2-tetralinyl)acetic acid (8.8 g) was dissolved in a mixed solution of THF (150 ml) and acetonitrile (50 ml), then piperidine (5.2 g), WSC (12 g), HOBt (6.0 g) and triethylamine (17 ml) were added to the solution, which was stirred at room temperature for 12 hours. Water was added to the reaction mixture, and extraction was conducted using ethyl acetate. The organic layer was washed with 1N hydrochloric acid, water, saturated sodium bicarbonate solution, water, and saturated aqueous sodium chloride solution, dried, and then concentrated. The residue was purified using silica gel chromatography (development solvent; ethyl acetate) to give the titled compound (10.3 g). Recrystallization from hexane gave crystals of the following melting points.

Workup

  1. washThe organic layer was washed with 1N hydrochloric acid, water, saturated sodium bicarbonate solution, water, and saturated aqueous sodium chloride solution
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified

Sources & evidence

ORD record
ord-1a6a000571a1438c8e0d6ebcff57eb0d
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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