Ammonia → HCID 20333084, compound

HRID 1706928Notes

Reaction equation

HRID 1706928 reaction equation
[CH2:1]=O.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][CH:22]=1)[C:8]([NH:10][C:11]([NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)=[O:12])=[O:9].[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]=[C:7]([CH:20]=[CH:21][CH:22]=1)[C:8]([NH:10][C:11](=[O:12])[NH:13][CH:14]1[CH2:19][CH2:18][N:17]([CH2:1][C:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[NH:23][CH:24]=2)[CH2:16][CH2:15]1)=[O:9]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 712FormaldehydeHCID 798IndoleHCID 19762401HCID 19762401, compound

Product 1

HCID 20333084HCID 20333084, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of formaldehyde (0.4 cm3, 40% aqueous solution) was added to a stirred solution of 1-(3methoxy benzoyl)-3-(piperid-4-yl)urea (1.39 g, 5 mmol) and indole (0.6 g, 5 mmol) in acetic acid (3 cm3). The solution was allowed to stand for 5 hours then diluted with water (50 cm3), basified by addition of ammonia and the precipitated product collected, washed with water, and dried yielding the title compound as the free base (2.1 g). The base was dissolved in hot ethanol (30 cm3), cooled, and acidified with ethanolic hydrogen chloride to precipitate the hydrochloride (2.3 g, 100%). Recrystallisation from aqueous methanol (60% methanol, 70 cm3) gave 1.8 g (81%) m.p. 234°-5° C.

Workup

  1. customthe precipitated product collected
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-4875602bc3744fea83538905c54e9f2e
Source dataset
uspto-grants-1980_06
Patent number
US04209521

Reaction notes

Loading…