Ammonia → HCID 18388210, compound

HRID 1941212Notes

Reaction equation

HRID 1941212 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, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Potassium cyanate (4.9 g) was 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-indol (10.8 g) (Pat. Appl. No. WO 9215302, Chem. Abstr. 117 (1992) 247029) in dichloromethane (100 ml) was added dropwise followed by stirring for 6 h at room temperature. Water (100 ml) was added and the reaction mixture made alkaline with conc. ammonia. The phases were separated followed by extraction with dichloromethane. The combined organic phases were dried over magnesium sulfate. Removal of solvent in vacuo gave a heavy oil which was purified by flash chromatography (silica gel, eluent: triethylamine/methanol/ethyl acetate 5:20:75). The title compound was isolated as a crystalline material, mp. 161°-63° C. Yield: 7.9 g.

Workup

  1. customThe phases were separated
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. customRemoval of solvent in vacuo
  5. customgave a heavy oil which
  6. customwas purified by flash chromatography (silica gel, eluent: triethylamine/methanol/ethyl acetate 5:20:75)

Sources & evidence

ORD record
ord-9c88b3d2b38a442bbe620df48b0752a8
Source dataset
uspto-grants-1997_12
Patent number
US05703087

Reaction notes

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