1,2-Dichloroethane → 4-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-iodobenzamide

HRID 854099

Reaction equation

HRID 854099 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH:9]2[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]2)[CH2:5]1.[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][C:14]=1[I:22].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[NH2:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([NH:3][CH:4]2[CH:9]3[CH2:10][CH2:11][N:6]([CH2:7][CH2:8]3)[CH2:5]2)=[O:18])=[CH:15][C:14]=1[I:22]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 164614-Amino-3-iodobenzoic AcidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 197853Quinuclidine, 3-amino-, dihydrochloride

Product 1

HCID 589329434-Amino-N-(1-azabicyclo[2.2.2]oct-3-yl)-3-iodobenzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2.04 g (10.3 mmol) of 3-aminoquinuclidine dihydrochloride, 2.70 g (10.3 mmol) of 4-amino-3-iodobenzoic acid, 1.39 g (10.3 mmol) of HOBt, 2.16 g (11.3 mmol) of EDC and 6.63 g (51.3 mmol) of N,N-diisopropylethylamine in 150 ml of DMF was stirred at room temperature for 16 h. 300 ml of water were added, and the aqueous phase was extracted three times with 300 ml of ethyl acetate each time. The combined organic phases were dried over sodium sulfate and the solvent was distilled off in vacuo. The residue was purified on a flash column (mobile phase: dichloromethane/methanol/triethylamine 90:10:0.2). 3.45 g (87%) of the desired title compound were obtined.

Workup

  1. extractionthe aqueous phase was extracted three times with 300 ml of ethyl acetate each time
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. distillationthe solvent was distilled off in vacuo
  4. customThe residue was purified on a flash column (mobile phase: dichloromethane/methanol/triethylamine 90:10:0.2)

Sources & evidence

ORD record
ord-cf406bb05eee4892a96ab2106020c65f
Source dataset
uspto-grants-2007_08
Patent number
US07256288B2

Linked notes

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