Ammonia → HCID 18388210, compound

HRID 2296739Notes

Reaction equation

HRID 2296739 reaction equation
[O-:1][C:2]#[N:3].[K+].FC(F)(F)C(O)=O.[NH2:12][CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([Cl:30])[CH:28]=3)[N:23]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[CH:22]=2)[CH2:17][CH2:16]1.N>ClCCl.O>[Cl:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][CH:26]=1)[N:23]([C:31]1[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=1)[CH:22]=[C:21]2[CH:18]1[CH2:19][CH2:20][N:15]([CH2:14][CH2:13][NH:12][C:2]([NH2:3])=[O:1])[CH2:16][CH2:17]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 6422Trifluoroacetic acidHCID 11378442Potassium cyanateHCID 18388212HCID 18388212, compound

Product 1

HCID 18388210HCID 18388210, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Potassium cyanate (4.9 g) is suspended in dichloromethane (50 ml) followed by dropwise addition of trifluoroacetic acid (4.4 ml) at 0° C. A solution of 3-[1-(2-aminoethyl)piperidin-4-yl]-5-chloro-1-(4-fluorophenyl)- 1H-indole (10.8 g) prepared according to Example 1 in dichloromethane (100 ml) is added dropwise followed by stirring for 6 hours at room temperature. Water (100 ml) is added and the reaction mixture is made alkaline with concentrated ammonia. The phases are separated, followed by extraction with dichloromethane. The combined organic phases are dried over magnesium sulfate. Removal of solvent under vacuum gives a heavy oil which is purified by flash chromatography (silica gel, eluent: triethylamine/methanol/ethyl acetate 5:20:75). About 7.9 g of the title compound is isolated as a crystalline material.

Workup

  1. additionis added dropwise
  2. customThe phases are separated
  3. extractionfollowed by extraction with dichloromethane
  4. dry with materialThe combined organic phases are dried over magnesium sulfate
  5. customRemoval of solvent under vacuum
  6. customgives a heavy oil which
  7. customis purified by flash chromatography (silica gel, eluent: triethylamine/methanol/ethyl acetate 5:20:75)

Sources & evidence

ORD record
ord-cd1806253ed94cdcba59c626deb74915
Source dataset
uspto-grants-2002_12
Patent number
US06489341B1

Reaction notes

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