Formaldehyde → HCID 9969663, compound

HRID 1368060Notes

Reaction equation

HRID 1368060 reaction equation
[C:1]1([C:11]([C:13]2[N:17]([CH3:18])[CH:16]=[C:15]([C:19](=[O:21])[CH3:20])[CH:14]=2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[CH2:29]=O.[OH-].[Na+]>CO>[C:1]1([C:11]([C:13]2[N:17]([CH3:18])[CH:16]=[C:15]([C:19](=[O:21])[CH2:20][CH2:29][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:14]=2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 2723721Piperidine, hydrochloride (1:1)HCID 18519859HCID 18519859, compound

Product 1

HCID 9969663HCID 9969663, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.5 g (0.005 moles) of 1-[5-(1-naphthalenoyl)(1-methyl-1H-pyrrol-3-yl)]-1-ethanone, 1.1 g (0.0065 mole) of piperidine hydrochloride, and 1.0 g (0.0065 mole) paraformaldehyde in 50 mL of MeOH was heated at 65° C. for 48 h and stirred 72 h at room temperature, the reaction mixture was poured into 3N NaOH and extracted with Et2O. The organics were washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo and the residue chromatographed on silica gel (95:5:0.5 CH2Cl2:MeOH:NH4OH). The resulting oil was treated with ethereal HCl to give 1.52 g (74%) of Compound 8. mp 141-143° C. CIMS m/z 375 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 8.2 (Ar, 2H); 8.1-7.95 (Ar, 2H); 7.75-7.5 (Ar, 4H); 6.85 (Ar, 1H); 4.15 (s, 3H); 3.45-3.2 (m, 6H); 2.8 (bq, 2H); 1.7 (m, 5H); 1.85 (m, 1H). Anal calc'd for: C24H26N2O2.HCl.0.4H2O: Theory: C, 68.94; H,6.70; N, 6.70. Found: C, 69.12; H, 6.55; N, 6.70; KF water 1.63.

Workup

  1. extractionextracted with Et2O
  2. washThe organics were washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent was evaporated in vacuo
  5. customthe residue chromatographed on silica gel (95:5:0.5 CH2Cl2:MeOH:NH4OH)
  6. additionThe resulting oil was treated with ethereal HCl

Sources & evidence

ORD record
ord-5f8e68ad2f074b3abae75ba9224709b6
Source dataset
uspto-grants-2003_06
Patent number
US06573267B2

Reaction notes

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