3-Pyridinecarboxaldehyde → HCID 178518599, compound

HRID 2294930Notes

Reaction equation

HRID 2294930 reaction equation
[N:1]1([C@H:7]2[CH2:12][CH2:11][C@H:10]([N:13]3[C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=4[NH:15][C:14]3=[O:22])[CH2:9][CH2:8]2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=O)[CH:24]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl.C(O)(=O)C.ClCCCl>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:4]2[CH2:3][CH2:2][N:1]([C@H:7]3[CH2:12][CH2:11][C@H:10]([N:13]4[C:17]5[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=5[NH:15][C:14]4=[O:22])[CH2:9][CH2:8]3)[CH2:6][CH2:5]2)[CH:24]=1

Participants

8

Reactant 4

HCID 103713-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 178518598HCID 178518598, compound

Product 1

HCID 178518599HCID 178518599, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.10 g of trans-1,3-dihydro-1-{4-(1-piperazinyl)-1-cyclohexyl}-2H-benzimidazol-2-one, 0.037 mL of 3-pyridinecarboxaldehyde, 15 mL of 1,2-dichloroethane, 0.10 mL of glacial acetic acid and 0.11 g of sodium triacetoxyborohydride was stirred at room temperature for 24 h. The reaction mixture was poured into 10 mL dichloromethane and 10 mL saturated aqueous NaHCO3 and the layers separated. The aqueous layer was extracted with 2×10 mL of dichloromethane and the combined organic layers dried over MgSO4 and concentrated under reduced pressure. Preparative thin layer chromatography on silica gel, eluting with 90:10:2 chloroform: methanol: conc. NH4 OH gave 0.050 g of trans-1,3-dihydro-1-{4-[4-(3-pyridinylmethyl)piperazin-1-yl]-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: mp=250° C.; 1H NMR (400 MHz, CDCl3) 9.71 (br s, 1H), 8.54 (dd, 2H), 7.68 (d, J=7.9, 1H), 7.26 (t, 1H), 7.15-7.02 (m, 4H), 4.26 (m, 1H), 3.54 (s, 2H), 2.66 (br dd, 4H), 2.27 (q, 2H), 2.10 (d, 2H), 1.97 (d, 2H), 1.92 (q, 2H): Analysis calculated for C23H29N5O.0.45 CHCl3C: 63.25, H: 6.67, N: 15.73 found C: 62.96, H: 6.74, N: 15.54.

Workup

  1. customthe layers separated
  2. extractionThe aqueous layer was extracted with 2×10 mL of dichloromethane
  3. dry with materialthe combined organic layers dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washPreparative thin layer chromatography on silica gel, eluting with 90:10:2 chloroform

Sources & evidence

ORD record
ord-5dde43e879324447a95fb1d77def673a
Source dataset
uspto-grants-1997_11
Patent number
US05691323

Reaction notes

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