Acetic Acid → HCID 1530394, compound

HRID 2241976Notes

Reaction equation

HRID 2241976 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[O:26][CH3:27])[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C(O)(=O)C>C(O)C.[Pd]>[CH3:27][O:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[N:17]1[CH2:16][CH2:15][N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:19][CH2:18]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 1070048HCID 1070048, compound

Product 1

HCID 1530394HCID 1530394, compoundYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 4-(1-benzylpiperidine-4-yl)-1-(2-methoxyphenyl)piperazine (Step 1, 20.0 g) in ethanol (120 mL) containing acetic acid (12 mL) was hydrogenated over 10% palladium on carbon (1 g) at 50 psig on a Parr apparatus for 12 hours. The catalyst was removed by filtration through Celite and the mixture was concentrated to dryness on a rotary evaporator. The residue was partitioned between chloroform and saturated aqueous NaHCO3. The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated on a rotary evaporator to provide the desired product (14.4 g) as a yellow oil which was used without further purification. The compound was characterized as the dihydrochloride salt, which was formed by dissolving the oil in ethanol and treating it with an excess of 1N HCl/Et2O to give an off-white precipitate, which was collected by vacuum filtration, washed with Et2O and dried in vacuo; MP. 274-288° C.; MS (ES) m/z (relative intensity): 276 (M+H)+ (100).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe mixture was concentrated to dryness on a rotary evaporator
  3. customThe residue was partitioned between chloroform and saturated aqueous NaHCO3
  4. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-8a3a3b254fc8496ca1739fb4bf3daab4
Source dataset
uspto-grants-2010_03
Patent number
US07671056B2

Reaction notes

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