Triethylamine → Epsiprantel

HRID 543123Notes

Reaction equation

HRID 543123 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[O:10]=[C:11]1[N:16]2[CH2:17][CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[CH:15]2[CH2:14][NH:13][CH2:12]1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH:1]1([C:7]([N:13]2[CH2:12][C:11](=[O:10])[N:16]3[CH2:17][CH2:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[CH:15]3[CH2:14]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 14547364HCID 14547364, compound

Product 1

HCID 72026EpsiprantelYield 64%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

Cyclohexanoyl chloride (0.34 g) was added to a solution of 4-oxo-1,2,3,4,6,7,8,12b-octahydropyrazino[2,1-a][2]benzazepine (0.5 g) in chloroform (20 ml, ethanol-free) maintained at 0° C. and triethylamine (0.26 g) added. The mixture was maintained at 0° C. for 30 min then at room temperature for 5 h. The solution was washed with, first, dilute hydrochloric acid and secondly with sodium bicarbonate solution. The chloroform solution was dried (MgSO4) and evaporated. The residue was recrystallised from chloroform/40°-60° C. petroleum ether to give white crystals of the title compound (0.48 g, 64%) m.p. 187°-90° C.

Workup

  1. temperatureThe mixture was maintained at 0° C. for 30 min
  2. washThe solution was washed with, first, dilute hydrochloric acid
  3. dry with materialThe chloroform solution was dried (MgSO4)
  4. customevaporated
  5. customThe residue was recrystallised from chloroform/40°-60° C. petroleum ether

Sources & evidence

ORD record
ord-f37a048fa46c4673a64b47780deedd43
Source dataset
uspto-grants-1987_04
Patent number
US04661489

Reaction notes

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