Sodium Carbonate → HCID 178473349, compound

HRID 1899900Notes

Reaction equation

HRID 1899900 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:9]2=[O:17])[CH2:4][CH2:3]1.[NH2:18][CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCCl>[CH2:28]([O:27][C:25]([N:22]1[CH2:21][CH2:20][CH:19]([NH:18][C@H:2]2[CH2:7][CH2:6][C@H:5]([N:8]3[C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=4[NH:10][C:9]3=[O:17])[CH2:4][CH2:3]2)[CH2:24][CH2:23]1)=[O:26])[CH3:29]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 214716841,3-dihydro-1-(4-oxocyclohexyl)-2H-benzimidazol-2-one

Product 1

HCID 178473349HCID 178473349, compoundYield 51.7%

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, 1.12 g of ethyl 4-amino-1-piperidinecarboxylate, 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 ethyl acetate gave 1.3 g of 1,3-dihydro-1-{trans-4-[1-ethoxycarbonyl-4-piperidinylamino]-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: 1H NMR (400 MHz, CDCl3) 9.8-9.9 (br m, 1H), 7.30 (m, 1H), 7.11-7.02 (m, 4H), 4.37 (m, 1H), 4.17-4.06 (m, 4H), 3.15 (m, 1H), 2.88 (t, 2H), 2.7 (m, 1H), 2.55 (m, 2H), 1.97 (d, 2H), 1.86 (d, 2H), 1.65 (q, 4H), 1.25 (m, 5H). Analysis calculated for C21H30N4O3C: 65.26, H: 7.82, N: 14.46 found C: 65.20, H: 7.57, N: 14.15.

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 ethyl acetate

Sources & evidence

ORD record
ord-dd2dd71579b949668334715ef3d985f9
Source dataset
uspto-grants-1996_11
Patent number
US05574044

Reaction notes

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