1,2-Dichloroethane → HCID 18407013, compound

HRID 1016442Notes

Reaction equation

HRID 1016442 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=[C:15]([CH3:31])[CH2:16][CH2:17][C:18]1[N:22]([CH2:23][CH2:24][C:25]#[N:26])[C:21]2[CH:27]=[CH:28][CH:29]=[CH:30][C:20]=2[N:19]=1.ClCCCl.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH:15]([CH3:31])[CH2:16][CH2:17][C:18]2[N:22]([CH2:23][CH2:24][C:25]#[N:26])[C:21]3[CH:27]=[CH:28][CH:29]=[CH:30][C:20]=3[N:19]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 317384-BenzylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 12359654HCID 12359654, compound

Product 1

HCID 18407013HCID 18407013, compoundYield 80.3%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 0.3 g of 4-benzyl-piperidine, 0.24 g of 3-[2-(3-oxo-butyl)-benzimidazol-1-yl]-propionitrile, 5 mL of 1,2-dichloroethane and 0.3 g of sodium triacetoxyborohydride was stirred at room temperature for 3 days. The reaction mixture was diluted with 50 mL chloroform and 10 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 magnesium sulfate and concentrated under reduced pressure. Low pressure chromatography eluting with a gradient of 80:20 ethyl acetate:methanol to 80:20:5 ethyl acetate:methanol:triethylamine gave 320 mg of 3-{2-[3-(4-benzyl-piperidin-1-yl)-butyl]-benzimidazol-1-yl}-propionitrile as a resin.

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 magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washLow pressure chromatography eluting with a gradient of 80:20 ethyl acetate

Sources & evidence

ORD record
ord-ee580dce9fb24356a6a7adde04f7c4c5
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Reaction notes

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