Water → HCID 178420091, compound

HRID 2293518Notes

Reaction equation

HRID 2293518 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.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][CH2:26][C:27]1[CH2:28]CNC[CH:32]=1.C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][CH2:26][C:27]1[CH2:28][CH2:19][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)[CH2:18][CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 214629694-(2-Furan-2-ylethyl)-1,2,3,6-tetrahydropyridineHCID 178483382HCID 178483382, compound

Product 1

HCID 178420091HCID 178420091, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-trimethylammonium iodide (0.42 g), 4-(2-furan-2-ylethyl)-1,2,3,6-tetrahydropyridine (0.20 g) and diisopropylethylamine (0.20 cm3) in DMF (10 cm3) was heated under argon at 90° C. for 24 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 to give a brown oil. Preparative thin layer chromatography on silica, eluting with 10% methanol-dichloromethane+1% ammonia, gave the title compound as a brown off, which was recrystallised as its half-oxalate salt from ethanol-hexane (0.083 g; 18%), m.p. 205°-208° C. (from EtOH-hexane); Found: C, 70.85; H, 6.5; N, 10.05. C23H25N3O.0.5(CO2H)2.0.2(H2O) requires C, 70.6; H, 6.5; N, 10.3%. δH (360 MHz; d6 -DMSO) 2.16 (2H, broad s, NCH2CH2), 2.27 (2H, t, J 7.7, --CH2 --), 2.67-2.73 (4H, m, 2 x --CH2 --), 2.86-2.90 (4H, m, 2 x --CH2 --), 3.22 (2H, broad s, NCH2CH=C), 3.88 (2H, broad s, --CH2N), 5.42 (1H, broad s, NCH2CH=C), 6.1 (1H, d, J 3, furyl-H3), 6.33 (1H, dd, J 3 and 2, furyl-H4), 7.18-7.29 (3H, m, 3 of ArH), 7.48 (1H, d, J 2, furyl-H5) and 7.64 (1H, d, J 6.6, 1 of ArH); m/z (CI+ ; NH3) 360 (MH+ ; 30%), 204 (50) and 174 (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. customto give a brown oil
  7. washPreparative thin layer chromatography on silica, eluting with 10% methanol-dichloromethane+1% ammonia

Sources & evidence

ORD record
ord-f915ad502570491098b2a8c49bbde051
Source dataset
uspto-grants-1997_11
Patent number
US05686480

Reaction notes

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