Water → HCID 178419879, compound

HRID 2293520Notes

Reaction equation

HRID 2293520 reaction equation
[I-].[NH:2]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([CH2:15][N+:16]([CH3:19])([CH3:18])C)=[N:3]1.[N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[N:30]1[CH2:35]CNC[CH2:31]1.C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[N:30]1[CH2:35][CH2:18][N:16]([CH2:15][C:4]2[C:5]3[CH2:6][CH2:7][C:8]4[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=4[C:10]=3[NH:2][N:3]=2)[CH2:19][CH2:31]1

Participants

6

Reactant 4

HCID 962WaterHCID 5011QuipazineHCID 81531DiisopropylethylamineHCID 178483382HCID 178483382, compound

Product 1

HCID 178419879HCID 178419879, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-trimethylammonium iodide (0.4 g), 1-(quinolin-2-yl)piperazine (0.23 g) and diisopropylethylamine (0.30 cm3) in DMF (10 cm3) was heated under argon at 80° C. for 48 hours. The mixture was cooled, poured into water (50 cm3) and extracted with 10% ethyl acetate-diethyl ether (2×25 cm3). The extracts were dried (MgSO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 5% methanol-dichloromethane+1% ammonia, removed baseline material. Preparative thin layer chromatography on silica, eluting with 3% methanol-dichloromethane+1% ammonia, gave the title compound, which was crystallised as the oxalate salt from ethanol to give brown granules (0.026 g; 5%), m.p. 154°-155° C. (from EtOH); Found: C, 64.6; H, 5.5; N, 13.7. C25H25N5.1.25(CO2 H)2.0.15(H2O) requires C, 64.7; H, 5.5; N, 13.7%. δH (360 MHz; d6 -DMSO) 2.73 (2H, t, J 7.7, --CH2 --), 2.84 (4H, broad s, 2 x NCH2CH2N), 2.90 (2H, t, J 7.7, --CH2 --), 3.79 (4H, broad s, 2 x NCH2CH2N) 7.18-7.30 (5H, m, 5 of ArH), 7.51-7.59 (2H, m, 2 of ArH), 7.65 (1H, d, J 7.6, 1 of ArH), 7.71 (1H, d, J 7.9, 1 of ArH) and 8.06 (1H, d, J 9.2, 1 of ArH); m/z (CI+ ; NH3) 396 (MH+ ; 40%) and 214 (100).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 10% ethyl acetate-diethyl ether (2×25 cm3)
  3. dry with materialThe extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washFlash column chromatography on silica gel, eluting with 5% methanol-dichloromethane+1% ammonia
  7. customremoved baseline material
  8. washPreparative thin layer chromatography on silica, eluting with 3% methanol-dichloromethane+1% ammonia

Sources & evidence

ORD record
ord-39e45d7165294cd5a1abd81192463c48
Source dataset
uspto-grants-1997_11
Patent number
US05686480

Reaction notes

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