Triethylamine → HCID 14547401, compound

HRID 543129Notes

Reaction equation

HRID 543129 reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[S: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](=[S: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 14547398HCID 14547398, compound

Product 1

HCID 14547401HCID 14547401, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Cyclohexanoyl chloride (0.16 g) was added to a mixture of 4-thioxo-1,2,3,4,6,7,8,12b-octahydropyrazino[2,1-a][2]benzazepine (0.24 g) and triethylamine (0.25 ml) in chloroform (20 ml, ethanol-free) at 0°. The mixture was maintained at 0° for 30 min then at room temperature for 5 hr. 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 purified by column chromatography (SiO2, Et2O) and recrystallised from dichloromethane/40°-60° C. petroleum ether to give white crystals of the title compound (55 mg, 16%) m.p. 150°-151° C.

Workup

  1. temperatureThe mixture was maintained at 0° 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 purified by column chromatography (SiO2, Et2O)
  6. customrecrystallised from dichloromethane/40°-60° C. petroleum ether

Sources & evidence

ORD record
ord-016b915f77bf450493bf829a6b89dee5
Source dataset
uspto-grants-1987_04
Patent number
US04661489

Reaction notes

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