Lithium Hydroxide → HCID 68419034, compound

HRID 1869733Notes

Reaction equation

HRID 1869733 reaction equation
C[O:2][C:3](=[O:28])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[CH:7]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)[CH2:6]1.[Li+].[OH-]>C1COCC1.O.Cl>[Cl:17][C:14]1[CH:15]=[CH:16][C:11]([N:8]2[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:28])=[O:2])[CH2:6][CH:7]2[C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:27])([F:25])[F:26])=[CH:22][CH:23]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 76697391HCID 76697391, compound

Product 1

HCID 68419034HCID 68419034, compoundYield 47.1%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl{1-(4-chlorophenyl)-2-[4(trifluoromethyl)phenyl]piperidine-4-yl}acetate (34 mg, 0.08 mmol) in THF (2 ml) and H2O (2 ml) was treated with LiOH (19 mg, 0.8 mmol) and the mixture was stirred at room temperature for 20 hours. The reaction was diluted with hydrochloric acid (1N, 20 ml) and extracted with EtOAc (2×20 ml). The combined extracts were washed with brine (×1), then dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica, eluting with 7.5% MeOH/DCM give the acid as a clear gum (15 mg, 45%). 1H NMR (400 MHz, CD3OD) δ: 1.34-1.40 (1H, m), 1.54-1.67 (1H, m), 1.84-2.12 (3H, m), 2.24-2.30 (2H, m), 2.86 (1H, dt, J 12.1, 2.4), 3.47-3.54 (1H, m), 4.15 (1H, dd, J 11.5, 2.7), 6.95 (2H, d, J 8.8), 7.06 (2H, d, J 8.8), 7.44 (4H, s).

Workup

  1. extractionextracted with EtOAc (2×20 ml)
  2. washThe combined extracts were washed with brine (×1)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica
  7. washeluting with 7.5% MeOH/DCM

Sources & evidence

ORD record
ord-621c9a42516845f5a87d73850dda0a5a
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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