Ammonia → HCID 20333087, compound

HRID 1706925Notes

Reaction equation

HRID 1706925 reaction equation
[CH2:1]=O.[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.[F:12][C:13]1[CH:30]=[CH:29][C:16]([C:17]([NH:19][C:20](=[O:28])[NH:21][CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:18])=[CH:15][CH:14]=1.N>C(O)(=O)C.O>[F:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][C:20]([NH:21][CH:22]2[CH2:23][CH2:24][N:25]([CH2:1][C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[NH:3][CH:4]=3)[CH2:26][CH2:27]2)=[O:28])=[O:18])=[CH:29][CH:30]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 798IndoleHCID 12608597HCID 12608597, compound

Product 1

HCID 20333087HCID 20333087, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Formaldehyde (0.4 cm3, 40% aqueous solution) was added to a stirred solution of indole (0.6 g, 0.005 mol) and 4-(4-fluorobenzoylureido)piperidine (1.33 g, 0.005 mol) in acetic acid (3 cm3). The reaction was allowed to stand for 5 hours then diluted with water (50 cm3). The turbid solution was basified by addition of ammonia and the precipitated solid collected by filtration, washed with water and ether to give 1.7 g (85%) of the title compound as the free base. The base was suspended in ethanol (10 cm3) and acidified with ethanolic hydrogen chloride. After stirring at room temperature for 0.5 hours and 0° C. for 0.5 hours the suspension was filtered to remove the hydrochloride. The hydrochloride was then dissolved in hot methanol acidified further with ethanolic hydrogen chloride and cooled to give the crystalline hydrochloride (1.4 g, 65.2%) double m.p. 210° C. and 260° C.

Workup

  1. filtrationthe precipitated solid collected by filtration
  2. washwashed with water and ether

Sources & evidence

ORD record
ord-31234dbd9935457ea6bf0ec254f71d70
Source dataset
uspto-grants-1980_06
Patent number
US04209521

Reaction notes

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