3,5-Dichlorophenyl isocyanate → HCID 9861625, compound

HRID 703407Notes

Reaction equation

HRID 703407 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-fc657b0a0263441d8cd83e21f2cbe1bd
Source dataset
uspto-grants-1991_01
Patent number
US04983600

Reaction notes

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