Benzylamine → 1-benzyl-2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole

HRID 456816Notes

Reaction equation

HRID 456816 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([C:13](=O)[CH2:14][CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O)[CH:7]=[CH:6]2.[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C(Cl)Cl>[CH2:25]([N:32]1[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:15][CH:14]=[C:13]1[C:8]1[CH:7]=[CH:6][C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH:9]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 184390201-(6-Methoxy-2-naphthyl)-4-phenylbutane-1,4-dione

Product 1

HCID 184390211-benzyl-2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrroleYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner as described in step 4 of Example 1, the title compound was prepared from 1-(6-methoxy-2-naphthyl)-4-phenylbutane-1,4-dione (0.300 g, 0.942 mmol), prepared in step 3 of Example 1, and benzyl amine (0.121 g, 1.13 mmol). The crude material was dissolved in methylene chloride and filtered through silica gel (95 g, 200–300 mesh). The solvent was removed under reduced pressure to give 1-benzyl-2-(6-methoxy-2-naphthyl)-5-phenyl-1H-pyrrole as a white solid (0.32 g, 87%), mp 152–153° C. Elemental Analysis for C28H23NO Calc'd: C, 86.34; H, 5.95; N, 3.60. Found: C, 85.46; H, 6.06; N, 3.58.

Workup

  1. filtrationfiltered through silica gel (95 g, 200–300 mesh)
  2. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-c58a4f897860458caeb6e8520aa58caf
Source dataset
uspto-grants-2007_03
Patent number
US07186749B2

Reaction notes

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