Formaldehyde → HCID 14625840, compound

HRID 2351862Notes

Reaction equation

HRID 2351862 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]=O.[CH2:9]([N:13]([CH2:35][CH2:36][CH2:37][CH3:38])[C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([OH:25])[CH:23]=2)[N:18]([CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:17]=1[CH3:34])=[O:15])[CH2:10][CH2:11][CH3:12]>C(O)(=O)C>[CH2:35]([N:13]([CH2:9][CH2:10][CH2:11][CH3:12])[C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([OH:25])[C:23]=2[CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[N:18]([CH2:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:17]=1[CH3:34])=[O:15])[CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8082PiperidineHCID 19844552HCID 19844552, compound

Product 1

HCID 14625840HCID 14625840, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Piperidine (11 g) and 11 g of 37% formalin were added to a solution of 44 g of N,N-dibutyl-5-hydroxy-2-methyl-1-(2-phenylethyl)indole-3-carboxamide in 20 m of acetic acid, and the mixture was stirred at 60° C. for 2 hours. The acetic acid was distilled off under reduced pressure. Water was added to the residue, which was made alkaline with potassium carbonate, followed by extraction with ethyl acetate. After the organic layer was washed with water and dried, the solvent was distilled off. Hexane was added to the residue to separate crystals. The crystals were collected by filtration and recrystallized from isopropyl ether to give 31 g of the titled compound as white crystals, m.p. 105°-107° C.

Workup

  1. distillationThe acetic acid was distilled off under reduced pressure
  2. additionWater was added to the residue, which
  3. extractionfollowed by extraction with ethyl acetate
  4. washAfter the organic layer was washed with water
  5. customdried
  6. distillationthe solvent was distilled off
  7. additionHexane was added to the residue
  8. customto separate crystals
  9. filtrationThe crystals were collected by filtration
  10. customrecrystallized from isopropyl ether

Sources & evidence

ORD record
ord-3ca1f8dd741647ff82fa5ec9ccb31c20
Source dataset
uspto-grants-1989_10
Patent number
US04874759

Reaction notes

Loading…