Triethylamine → 1-Amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran

HRID 5884

Reaction equation

HRID 5884 reaction equation
[NH2:1][C:2]1[C:10]2[CH:9]3[CH2:11][CH2:12][CH2:13][CH2:14][CH:8]3[O:7][C:6]=2[C:5](C(O)=O)=[CH:4][C:3]=1[Cl:18].C(N(CC)CC)C.C(OC(Cl)=O)C.Cl.Cl.NC1C2CCN(CC2)C1>C(Cl)(Cl)Cl.O>[NH2:1][C:2]1[C:10]2[CH:9]3[CH2:11][CH2:12][CH2:13][CH2:14][CH:8]3[O:7][C:6]=2[CH:5]=[CH:4][C:3]=1[Cl:18]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 151360481-Amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid

Product 1

HCID 197944301-Amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent3×

Procedure

To a cold solution of 0.3 g 1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-carboxylic acid in 40 ml chloroform is added 0.3 g of triethylamine and then 0.2 g ethylchloroformate in 10 ml chloroform. Stirring is continued for 2 hours. This is then added to a cold mixture of 3 g 3-aminoquinuclidine dihydrochloride in 20 ml water containing 7.5 g K2CO3. Stirring is continued overnight. The reaction mixture is then diluted with chloroform, the two layers separated and the chloroform layer washed twice with water, dried over magnesium sulfate, filtered and evaporated to dryness to give 1-amino-2-chloro-5a,6,7,8,9,9a-hexahydrodibenzofuran-4-(N-1-azabicyclo [2.2.2.]oct-3-yl)carboxamide as an oily Product.

Workup

  1. stirringStirring
  2. waitis continued overnight
  3. customthe two layers separated
  4. washthe chloroform layer washed twice with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-16679a0222a54903abc287b1b5d2fb96
Source dataset
uspto-grants-1993_09
Patent number
US05246942

Linked notes

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