Triethylamine → HCID 178519685, compound

HRID 1899902Notes

Reaction equation

HRID 1899902 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C@H:8]2[CH2:13][CH2:12][C@H:11]([N:14]3[C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[NH:16][C:15]3=[O:23])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1.C(N(CC)CC)C.Cl.[C:32](Cl)(=[O:39])[C:33]1[CH:38]=[CH:37][CH:36]=[N:35][CH:34]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[N:35]1[CH:36]=[CH:37][CH:38]=[C:33]([C:32]([N:1]2[CH2:2][CH2:3][CH:4]([NH:7][C@H:8]3[CH2:9][CH2:10][C@H:11]([N:14]4[C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=5[NH:16][C:15]4=[O:23])[CH2:12][CH2:13]3)[CH2:5][CH2:6]2)=[O:39])[CH:34]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 178518600HCID 178518600, compound

Product 1

HCID 178519685HCID 178519685, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 0.050 g of 1,3-dihydro-1-{trans-4-[4-piperidinylamino]-1-cyclohexyl}-2H-benzimidazol-2-one and 0.023 mL of triethylamine in 1.5mL of dichloromethane was added 0.024 g of nicotinoyl chloride hydrochloride. After 12 h, 20 mL of saturated sodium carbonate was added, the organic layer was separated, and the aqueous layer extracted with two addtional 20 mL portions of chloroform. The combined organic extracts dried over MgSO4 and concentrated under reduced pressure. Chromatography over silica gel eluting with 10% methanol/10% conc. NH4OH in chloroform gave 0.024 g of 1,3-dihydro-1-{trans -4-[1-(3-pyridinecarbonyl)-4-piperidinylamino]-1-cyclohexyl}-2H-benzimidazol-2-one as a white solid: 1H NMR (400 MHz, CDCl3) 9.04 (s, 1H), 8.68 (dd, 2H), 7.77 (m, 1H), 7.38 (m, 1H), 7.26 (m, 1H), 7.06 (m, 3H), 4.67 (br s, 1H), 3.75 (br s, 1H), 3.18 (br s, 2H), 2.99 (br s, 1H), 2.87 (br s, 1H), 2.55 (q, 2H), 2.13-1.9 (m, 4 H), 1.72-1.3 (m, 7H). The dihydrochloride salt was precipitated from chloroform/ethyl acetate: Analysis calculated for C24H29N5O2.2HCl.0.90 CHCl3.0.25 CH3CO2CH2CH3C: 50.02, H: 5.95, N: 11.26 found C: 51.28, H: 5.49, N: 11.53.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous layer extracted with two addtional 20 mL portions of chloroform
  3. dry with materialThe combined organic extracts dried over MgSO4
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d4a460c8d76e423baaf4a78ac52a7343
Source dataset
uspto-grants-1996_11
Patent number
US05574044

Reaction notes

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