3,5-Dichlorophenyl isocyanate → HCID 9861625, compound

HRID 1030474Notes

Reaction equation

HRID 1030474 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH:14]([NH2:20])[CH2:13]2>C1(C)C=CC=CC=1.C1COCC1>[N:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[CH:14]([NH:20][C:10]([NH:9][C:4]1[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=1)=[O:11])[CH2:13]2

Participants

5

Reactant 2

HCID 944603,5-Dichlorophenyl isocyanateHCID 1232383-Aminoquinuclidine

Product 1

HCID 9861625HCID 9861625, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,5-dichlorophenyl isocyanate (1.88 g, 10 mmol) in toluene (20 ml) was added at 0° to 1-azabicyclo[2.2.2]octan-3-amine (3-aminoquinuclidine) (1.26 g, 10 mmol) in THF (40 ml). The mixture was stirred at room temperature overnight and evaporated to dryness. The residue was partitioned between ether and dilute hydrochloric acid. The aqueous phase was basified with potassium carbonate and extracted with ethyl acetate. The dried (Na2SO4)ethyl acetate phase was evaporated and the residue (1.64 g) converted to the 1:1 oxalate, quarter hydrate, mp 208°-209° C. (dec).

Workup

  1. customevaporated to dryness
  2. customThe residue was partitioned between ether and dilute hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. customThe dried (Na2SO4)ethyl acetate phase was evaporated

Sources & evidence

ORD record
ord-5229a8c981554237857a70ecb41eeffa
Source dataset
uspto-grants-1992_04
Patent number
US05106843

Reaction notes

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