Triethylamine → HCID 86739999, compound

HRID 1381157Notes

Reaction equation

HRID 1381157 reaction equation
[C:1]1([C@@:7]23[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C@@H:8]2[CH2:9][NH:10][CH2:11][CH2:12]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH:27]1([C:30](Cl)=[O:31])[CH2:29][CH2:28]1>C(Cl)(Cl)Cl>[CH:27]1([C:30]([N:10]2[CH2:11][CH2:12][C@:7]3([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[O:15][C:14]4[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=4[C@@H:8]3[CH2:9]2)=[O:31])[CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 86739997HCID 86739997, compound

Product 1

HCID 86739999HCID 86739999, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a solution of 3.77 g of cis-1,2,3,4,4a,9b-hexahydro-4a-phenyl-benzofuro[3,2-c]pyridine in 100 ml of chloroform containing 1.67 g of triethylamine was added dropwise with stirring under nitrogen a solution of 1.65 g of cyclopropane carbonyl chloride in 25 ml of chloroform. The reaction mixture was stirred at room temperature for 4 hours, diluted with 100 ml of chloroform and washed with 100 ml of 2N HCl and 100 ml of 10% aqueous NaOH. The organic layer was dried over anhydrous Na2SO4 and evaporated in vacuo to afford 4.70 g (98.1%) of a glass.

Workup

  1. washwashed with 100 ml of 2N HCl and 100 ml of 10% aqueous NaOH
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-1e10160a2fb547b2bd55f2ad2917ac1f
Source dataset
uspto-grants-1986_04
Patent number
US04585779

Reaction notes

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