Sodium Carbonate → HCID 21471545, compound

HRID 2294931Notes

Reaction equation

HRID 2294931 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[O:13]=[C:14]1[N:18]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[NH:15]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCl.C(O)(=O)C.ClCCCl>[O:13]=[C:14]1[N:18]([CH:19]2[CH2:20][CH2:21][N:22]([CH:2]3[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]3)[CH2:23][CH2:24]2)[C:17]2[CH:25]=[CH:26][CH:27]=[CH:28][C:16]=2[NH:15]1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 21471545HCID 21471545, compoundYield 65.9%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 4-oxocyclohexanecarboxylate (1.86 g), 4-(2-oxo-1-benzimidazolinyl)piperidine (1.98 g), 1,2-dichloroethane (40 mL), glacial acetic acid (0.52 mL) and sodium triacetoxyborohydride (3.47 g) was stirred at room temperature for 72 h. The reaction mixture was poured into dichloromethane (50 mL) and saturated Na2CO3 (50 mL) and the layers separated. The aqueous layer was extracted with 2×50 mL of dichloromethane and the combined organic layers dried over MgSO4 and concentrated to dryness under reduced pressure. The crude product was purified by flash column chromatography on silica, eluting with a gradient of ethyl acetate; 0-8% methanol to yield the cis and trans isomers of ethyl 1-[4-(2-keto-1-benzimidazolinyl)piperidin-1-yl]cyclohexane4-carboxylate as a colorless solid (2.23 g).

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×50 mL of dichloromethane
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated to dryness under reduced pressure
  5. customThe crude product was purified by flash column chromatography on silica
  6. washeluting with a gradient of ethyl acetate

Sources & evidence

ORD record
ord-6d8166e62366472399e24ab2db5c207a
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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