Water → HCID 178468979, compound

HRID 1816339Notes

Reaction equation

HRID 1816339 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:4][CH2:3]1.F[C:15]1[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[CH3:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[CH2:13][CH2:12][N:11]([C:15]3[CH:25]=[CH:24][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:17][CH:16]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:7]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 178461287HCID 178461287, compound

Product 1

HCID 178468979HCID 178468979, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of cis-1-(4-methylcyclohexyl)piperazine (29.6 g), ethyl 4-fluorobenzoate (41.0 g) and potassium carbonate (67.3 g) in DMSO (300 ml) was stirred at 140° C. for 9 hours. The reaction mixture was poured into water (1.2 l) and extracted twice with ethyl acetate (400 ml). The extracts were collected, washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The resulting residue was chromatographed on silica gel (1 l) eluting with a mixture of n-hexane and ethyl acetate (2:1 v/v). The fractions containing the desired compound were collected and evaporated under reduced pressure to give ethyl 4-[cis-4-(4-methylcyclohexyl)-1-piperazinyl]benzoate (37.64 g).

Workup

  1. extractionextracted twice with ethyl acetate (400 ml)
  2. customThe extracts were collected
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe resulting residue was chromatographed on silica gel (1 l)
  7. washeluting with a mixture of n-hexane and ethyl acetate (2:1 v/v)
  8. additionThe fractions containing the desired compound
  9. customwere collected
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bdb2bf9adbdb48148604455ae2d381d0
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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