Ammonia → HCID 20333085, compound

HRID 1706924Notes

Reaction equation

HRID 1706924 reaction equation
[CH2:1]=O.[CH3:3][O:4][C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12](=[O:20])[NH:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:10])=[CH:7][CH:6]=1.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1.N>C(O)(=O)C.O>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([C:9]([NH:11][C:12](=[O:20])[NH:13][CH:14]2[CH2:19][CH2:18][N:17]([CH2:1][C:25]3[C:26]4[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=4)[NH:23][CH:24]=3)[CH2:16][CH2:15]2)=[O:10])=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 798IndoleHCID 12608612HCID 12608612, compound

Product 1

HCID 20333085HCID 20333085, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Formaldehyde (0.4 cm3, 40% aqueous solution) was added to a stirred solution of 4-(4-methoxybenzoylureido)piperidine (1.39 g, 0.005 mol) and indole (0.6 g, 0.005 mol) in acetic acid (3 cm3). The solution was allowed to stand for 5 hours and the diluted with water (50 cm3). The turbid solution was then basified by addition of ammonia solution and the precipitated solid collected by filtration washed with water and ether to give 2.1 g (95%) of the title compound as the free base. The base was suspended in warm ethanol (20 cm3) and acidified with ethanolic hydrogen chloride. After stirring at room temperature for 1 hour and 0° C. for 0.5 hours the suspension was filtered to remove the hydrochloride. The hydrochloride was recrystallised from aqueous methanol (80% methanol, 20 cm3) to give (1.8 g, 82%) of the hydrochloride of the title compound m.p. 220°-22° C.

Workup

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

Sources & evidence

ORD record
ord-a6e5a45c4e874403a43a857758cc9a60
Source dataset
uspto-grants-1980_06
Patent number
US04209521

Reaction notes

Loading…