1,2-Dichloroethane → HCID 835697, compound

HRID 1783779Notes

Reaction equation

HRID 1783779 reaction equation
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].C(Cl)CCl.[CH:11]1[CH:12]=[CH:13][C:14]2[N:19](O)N=[N:17][C:15]=2[CH:16]=1.NCC1C=CC=CN=1>C1COCC1>[N:17]1[CH:13]=[CH:12][CH:11]=[CH:16][C:15]=1[CH2:14][NH:19][C:1](=[O:6])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 264Butyric AcidHCID 195092-PyridinemethanamineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 835697HCID 835697, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of butyric acid (4.5 mL, 48.7 mmol) in THF (50 mL) was added EDC (11.2 g, 58.4 mmol) and HOBt (7.88 g, 58.4 mmol). The mixture was stirred for 10 min. then 2-(aminomethyl)pyridine (4.7 mL, 46.3 mmol) was added. The solution was allowed to stir for 3 h then quenched with water (100 mL). The mixture was extracted with ethyl acetate (2×100 mL) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to yield N-pyridin-2-ylmethyl-butyramide (5.82 g, 67%).

Workup

  1. stirringto stir for 3 h
  2. customthen quenched with water (100 mL)
  3. extractionThe mixture was extracted with ethyl acetate (2×100 mL)
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2be2ca97ad3e499caa174684a31156f4
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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