Propionic Acid → HCID 86606830, compound

HRID 1437678Notes

Reaction equation

HRID 1437678 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[C:30](O)(=[O:33])[CH2:31][CH3:32].CCN(CC)CC.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.O>[F:29][C:3]([F:2])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:30](=[O:33])[CH2:31][CH3:32])[CH2:11][C@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 1032Propionic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochloride

Product 1

HCID 86606830HCID 86606830, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (132 mg) obtained in Example 1, propionic acid (32 mg) and Et3N (0.083 ml) in DMF (5 ml), WSC.HCl (0.15 g) and HoBt.H2O (0.092 g) were added, and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into water, and then the product was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was purified by preparative HPLC to obtain the title compound as colorless amorphous.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated sodium hydrogen carbonate solution and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-3c7d2782492c406bb1bf2e1e609c4e15
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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