Hydrochloric Acid → 7-(3-Methoxycarbonylphenyl)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235136Notes

Reaction equation

HRID 235136 reaction equation
C[Sn](C)(C)[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[N:13]2[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]2)=[CH:5][CH:4]=1.[CH3:22][O:23][C:24]([C:26]1[CH:27]=[C:28](Br)[CH:29]=[CH:30][CH:31]=1)=[O:25].C(N(CC)CC)C.[Cl-].[Li+].Cl>CN(C=O)C.CCOCC.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:22][O:23][C:24]([C:26]1[CH:31]=[C:30]([C:3]2[CH:12]=[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=[C:10]3[N:13]3[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]3)=[CH:5][CH:4]=2)[CH:29]=[CH:28][CH:27]=1)=[O:25]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 12070Methyl 3-bromobenzoateHCID 433294Lithium ChlorideHCID 221156087-Trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene

Product 1

HCID 189675057-(3-Methoxycarbonylphenyl)-1-(4-methyl-1-piperazinyl)-naphthalene

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

The title product was prepared following the procedure of example 41 from 7-trimethylstannyl-1-(4-methyl-1-piperazinyl)-naphthalene (0.25 g, 0.67 mmol), 3-methoxycarbonyl-1-bromobenzene (0.16 g, 0.74 mmol), triethylamine (0.45 mL, 3.23 mmol), lithium chloride (0.088 g, 2.07 mmol), and bis (triphenylphosphine) palladium chloride (0.025 g, 0.036 mmol) in DMF (12.5 mL) with a heating time of 1.5 hours at 120 to 130° C. The product obtained was 0.15 g (63%) in yield as an oil which was converted to a hydrochloride salt with HCl gas in ether. The solid was collected under a nitrogen atmosphere and recrystallized from chloroform/ether for analysis: mp 201°-203° C.; 13C NMR δ 167.05, 147.37, 141.78, 137.80, 134.08, 131.87, 130.89, 129.57, 129.07, 128.63, 128.47, 126.28, 125.76, 125.02, 120.59, 116.85, 54.30, 52.33, 49.75, 43.70.

Workup

  1. customwith a heating time of 1.5 hours
  2. customat 120 to 130° C
  3. customThe product obtained
  4. customin yield as an oil which
  5. customThe solid was collected under a nitrogen atmosphere
  6. customrecrystallized from chloroform/ether for analysis

Sources & evidence

ORD record
ord-dfb157b8e6b649ff8c48d8e1b061deea
Source dataset
uspto-grants-1997_01
Patent number
US05597826

Reaction notes

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