1,2-Dichloroethane → HCID 18407007, compound

HRID 1016439Notes

Reaction equation

HRID 1016439 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=[CH:15][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.Cl[CH2:32]CCl.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]([CH2:15][CH2:16][CH: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)[CH3:32])[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 12017139HCID 12017139, compound

Product 1

HCID 18407007HCID 18407007, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 0.3 g of 4-benzyl-piperidine, 0.2 g of 3-[2-(3-oxo-propyl)-benzimidazol-1-yl]-propionitrile, 5 mL of 1,2-dichloroethane and 0.3 g of sodium triacetoxyborohydride was stirred at room temperature for 24 h. 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 70:30 ethyl acetate:methanol to 80:20:2 ethyl acetate:methanol:triethylamine gave 205 mg of 3-{2-[3-(4-benzyl-piperidin-1-yl)-1-methyl-propyl]-benzimidazol-1-yl }-propionitrile as a gum.

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 70:30 ethyl acetate

Sources & evidence

ORD record
ord-3fc9f78a2006452c907d69df7a65fe80
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Reaction notes

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