Sodium Carbonate → HCID 178523785, compound

HRID 1899904Notes

Reaction equation

HRID 1899904 reaction equation
C(O[C:6]([NH:8][CH:9]1[CH2:14][CH2:13][C:12](=O)[CH2:11][CH2:10]1)=[O:7])(C)(C)C.[O:16]=[C:17]1[N:21]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[C:20]2[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=2[NH:18]1.C(O[BH-](O[C:42](=O)[CH3:43])OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>O.O1CCCC1.ClCCCl.C(O)(=O)C>[N:8]1[CH:43]=[CH:42][CH:11]=[C:10]([C:6]([NH:8][C@@H:9]2[CH2:10][CH2:11][C@H:12]([N:25]3[CH2:24][CH2:23][CH:22]([N:21]4[C:20]5[CH:28]=[CH:29][CH:30]=[CH:31][C:19]=5[NH:18][C:17]4=[O:16])[CH2:27][CH2:26]3)[CH2:13][CH2:14]2)=[O:7])[CH:9]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 178523785HCID 178523785, compound

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N-tert-butyloxycarbonyl-4-aminocyclohexanone (1.32 g), 4-(2-keto-1-benzimidazolinyl)piperidine (1.48 g), sodium triacetoxyborohydride (1.97 g), acetic acid (0.35 mL), 1,2-dichloroethane (50 mL) and tetrahydrofuran (60 mL) was stirred at room temperature for 3 days. Saturated aqueous Na2CO3 (30 mL) and H2O (30 mL) were added and the mixture was extracted with dichloromethane (2×100 mL). The combined organic extracts were concentrated to dryness under reduced pressure. Column chromatography on silica gel, eluting with dichloromethane-10% methanol-1% NH4OH gave a mixture of the expected product isomers: 1,3-dihydro-1-{1-[trans-4-(tert-butyloxycarbonylamino)cyclohexyl]piperidin-4-yl}-2H-benzimidazol2-one and 1,3-dihydro-1-{1-[cis-4-(tert-butyloxycarbonylamino)cyclohexyl]piperidin-4-yl}-2H-benzimidazol2-one as a colorless solid (1.9 g).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×100 mL)
  2. concentrationThe combined organic extracts were concentrated to dryness under reduced pressure
  3. washColumn chromatography on silica gel, eluting with dichloromethane-10% methanol-1% NH4OH
  4. customgave

Sources & evidence

ORD record
ord-3d1ac3d0c2e44cfb9c1b03df7dbd5a73
Source dataset
uspto-grants-1996_11
Patent number
US05574044

Reaction notes

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