1,2-Dichloroethane → HCID 1722026, compound

HRID 1783776Notes

Reaction equation

HRID 1783776 reaction equation
[C:1]([OH:7])(=O)[CH2:2][CH2:3][CH2:4][CH3:5].C(Cl)CCl.[CH:12]1[CH:13]=[CH:14][C:15]2[N:20](O)N=[N:18][C:16]=2[CH:17]=1.NCC1C=CC=CN=1>C1COCC1>[N:18]1[CH:14]=[CH:13][CH:12]=[CH:17][C:16]=1[CH2:15][NH:20][C:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 7991Pentanoic AcidHCID 195092-PyridinemethanamineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 1722026HCID 1722026, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of pentanoic acid (5.3 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 pentanoic acid (pyridin-2-ylmethyl)-amide (8.60, 92%).

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-3d2ea128900d4133b011c310b8a71f54
Source dataset
uspto-grants-2009_03
Patent number
US07501438B2

Reaction notes

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