Potassium Carbonate → HCID 178504960, compound

HRID 1517661Notes

Reaction equation

HRID 1517661 reaction equation
C(N(CC1C=CC=CC=1)C1CCC(=O)CC1)C1C=CC=CC=1.CS(N1CCNCC1)(=O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[K+].[K+].C([N:60](CC1C=CC=CC=1)[C@H:61]1[CH2:66][CH2:65][C@H:64]([N:67]2[CH2:72][CH2:71][N:70]([S:73]([CH3:76])(=[O:75])=[O:74])[CH2:69][CH2:68]2)[CH2:63][CH2:62]1)C1C=CC=CC=1>ClCCl.CO.[Pd].O>[CH3:76][S:73]([N:70]1[CH2:69][CH2:68][N:67]([C@H:64]2[CH2:65][CH2:66][C@H:61]([NH2:60])[CH2:62][CH2:63]2)[CH2:72][CH2:71]1)(=[O:74])=[O:75]

Participants

10

Reactant 5

HCID 11430Potassium CarbonateHCID 7091611-(Methylsulfonyl)piperazineHCID 5049666Sodium triacetoxyborohydrideHCID 220099024-(Dibenzylamino)cyclohexan-1-oneHCID 178504961HCID 178504961, compound

Product 1

HCID 178504960HCID 178504960, compound

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

14 g (47 mmol) 4-dibenzylamino-cyclohexanone, 8.5 g (51 mmol) 1-methanesulphonyl-piperazine and 17.5 g (78 mmol) sodium triacetoxyborohydride are stirred in 250 ml dichloromethane for 4 hours at ambient temperature. Then the reaction mixture is combined with 200 ml of water and 20 g potassium carbonate. The organic phase is separated off, dried and evaporated to dryness. The residue is purified by chromatography. Yield: 4.8 g trans-isomer 4.8 g (11 mmol) trans-dibenzyl-[4-(4-methanesulphonyl-piperazin-1-yl)-cyclohexyl]-amine are dissolved in 100 ml of methanol and 2 g palladium/charcoal (10%) are added. The mixture is hydrogenated at 50 psi and 50° C. Then the catalyst is suction filtered, the mother liquor is concentrated by evaporation. The precipitate formed is suction filtered and washed with diethyl ether. Yield: 2.4 g

Workup

  1. customThe organic phase is separated off
  2. customdried
  3. customevaporated to dryness
  4. customThe residue is purified by chromatography
  5. customis hydrogenated at 50 psi and 50° C
  6. filtrationfiltered
  7. concentrationthe mother liquor is concentrated by evaporation
  8. customThe precipitate formed
  9. filtrationfiltered
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-014e4d8b0c284a41ac018d9fd810fdc5
Source dataset
uspto-grants-2012_07
Patent number
US08232286B2

Reaction notes

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