Formaldehyde → HCID 20333086, compound

HRID 1706923Notes

Reaction equation

HRID 1706923 reaction equation
[CH2:1]=O.[C:3]([NH:11][C:12](=[O:20])[NH:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:21][C:22]1[NH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2>C(O)(=O)C.O>[C:3]([NH:11][C:12]([NH:13][CH:14]1[CH2:15][CH2:16][N:17]([CH2:1][C:30]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][C:22]=2[CH3:21])[CH2:18][CH2:19]1)=[O:20])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 72242-MethylindoleHCID 126085824-Benzoylureidopiperidine

Product 1

HCID 20333086HCID 20333086, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of formaldehyde (1.6 cm3, 40% aqueous solution) was added to a stirred solution of 4-benzoylureidopiperidine (5 g, 0.02 mol) and 2-methylindole (2.6 g, 0.02 mol) in acetic acid (12 cm3). The solution was allowed to stand for 5 hours and diluted with water (100 cm3). The precipitated solid was removed by filtration and discarded. The filtrate was basified by addition of ammonia to precipitate the product which was collected by filtration. The product was triturated with ethanol, then recrystallised from a mixture of acetonitrile (120 cm3) and water (12 cm3) to give the title compound as the pure base (1.65 g, 21%) m.p. 209°-11° C.

Workup

  1. customThe precipitated solid was removed by filtration
  2. additionThe filtrate was basified by addition of ammonia
  3. customto precipitate the product which
  4. filtrationwas collected by filtration
  5. customThe product was triturated with ethanol
  6. customrecrystallised from a mixture of acetonitrile (120 cm3) and water (12 cm3)

Sources & evidence

ORD record
ord-294144e8da714e718abc929ef29402b2
Source dataset
uspto-grants-1980_06
Patent number
US04209521

Reaction notes

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