Triethylamine → HCID 86606831, compound

HRID 1437680Notes

Reaction equation

HRID 1437680 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.CCN(CC)CC.[N:37]([CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:38]=[O:39].C(=O)([O-])O.[Na+]>C1COCC1>[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:38]([NH:37][CH2:40][C:41]([O:43][CH2:44][CH3:45])=[O:42])=[O:39])[CH2:11][C@H:10]1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76283Ethyl isocyanatoacetateHCID 516892Sodium BicarbonateHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochloride

Product 1

HCID 86606831HCID 86606831, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (35 mg) obtained in Example 1 and Et3N (22 μl) in THF (2.0 ml), ethyl isocyanatoacetate (11 mg) was added at 0° C., and the reaction mixture was stirred at room temperature for 3 hours. To the reaction mixture, an aqueous saturated sodium hydrogen carbonate solution was added, and then the product was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried, and then the solvent was evaporated under reduced pressure, and the residue was purified by preparative HPLC to obtain the title compound.

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-960b7877402c451cac0bcce35895ba25
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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