Sodium Carbonate → HCID 178447193, compound

HRID 2294916Notes

Reaction equation

HRID 2294916 reaction equation
O=C1CCC(N2C3C=CC=CC=3NC2=O)CC1.N1(C(OC(C)(C)C)=O)CCNCC1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+].[C:51]([C:55]([N:57]1[CH2:62][CH2:61][N:60]([C@@H:63]2[CH2:68][CH2:67][C@H:66]([N:69]3[C:73]4[CH:74]=[CH:75][CH:76]=[CH:77][C:72]=4[NH:71][C:70]3=[O:78])[CH2:65][CH2:64]2)[CH2:59][CH2:58]1)=[O:56])([CH3:54])([CH3:53])[CH3:52]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCCl>[C:51]([C:55]([N:57]1[CH2:58][CH2:59][N:60]([C@H:63]2[CH2:64][CH2:65][C@H:66]([N:69]3[C:73]4[CH:74]=[CH:75][CH:76]=[CH:77][C:72]=4[NH:71][C:70]3=[O:78])[CH2:67][CH2:68]2)[CH2:61][CH2:62]1)=[O:56])([CH3:54])([CH3:52])[CH3:53]

Participants

9

Reactant 5

HCID 10340Sodium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 214716841,3-dihydro-1-(4-oxocyclohexyl)-2H-benzimidazol-2-oneHCID 178447192HCID 178447192, compound

Product 1

HCID 178447193HCID 178447193, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 1.5 g of 1,3-dihydro-1-(4-oxocyclohexyl)-2H-benzimidazol-2-one, 1.21 g of tert-butyl 1-piperazinecarboxylate, 20 mL of 1,2-dichloroethane, 0.40 mL of glacial acetic acid and 1.79 g of sodium triacetoxyborohydride was stirred at room temperature for 48 h. The reaction mixture was poured into 50 mL chloroform and 50 mL saturated aqueous Na2CO3 and the layers separated. The aqueous layer was extracted with 2×25 mL of chloroform and the combined organic layers dried over MgSO4 and concentrated under reduced pressure. Chromatography of the crude product on silica gel, eluting with 10% methanol in chloroform gave, firstly, 0.63 g of 1,3-dihydro-1-{cis-4-[4-(tert-butylcarbonyl)piperazin-1-yl]-1-cyclohexyl}-2H-benzimidazol-2-one: 1H NMR (400 MHz, CDCl3) 7.47 (m, 1H), 7.25 (m, 1H), 7.05 (m, 2H), 4.55 (m, 1H), 3.54 (m, 4H), 2.49 (m, 6H), 2.27 (s, 0.8H), 2.15 (d, 2H), 1.97 (m, 0.2H), 1.57 (m, 4H), 1.49 (s, 9H). Later fractions gave 1,3-dihydro-1-{trans-4-[4-(tert-butylcarbonyl)piperazin-1-yl]-1-cyclohexyl}-2H-benzimidazol-2-one: 1H NMR (400 MHz, CDCl3) 7.15 (m, 2H), 7.06 (m, 2H), 4.28 (m, 1H), 3.46 (m, 4H), 2.56 (m, 4H), 2.5 (m, 1H), 2.26 (m, 2H), 2.03 (m, 6H), 1.47 (s, 9H).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×25 mL of chloroform
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washChromatography of the crude product on silica gel, eluting with 10% methanol in chloroform
  6. customgave

Sources & evidence

ORD record
ord-89268bddb2e84cb2bb9f4de60914e200
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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