Water → HCID 178420082, compound

HRID 2293521Notes

Reaction equation

HRID 2293521 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.[C:20]1(/[CH:26]=[CH:27]/[C:28]2[CH2:29]CNC[CH:33]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(C(C)C)CC)(C)C.O>CN(C=O)C>[C:20]1(/[CH:26]=[CH:27]/[C:28]2[CH2:29][CH2:19][N:16]([CH2:15][C:4]3[C:5]4[CH2:6][CH2:7][C:8]5[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=5[C:10]=4[NH:2][N:3]=3)[CH2:18][CH:33]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 15342358(E)-4-(2-phenylethenyl)-1,2,3,6-tetrahydropyridineHCID 178483382HCID 178483382, compound

Product 1

HCID 178420082HCID 178420082, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-trimethylammonium iodide (0.20 g), 4-((E)-2-phenylethenyl)-1,2,3,6-tetrahydropyridine (0.085 g) and diisopropylethylamine (0.10 cm3) in DMF (10 cm3) was heated under nitrogen at 80° C. for 48 hours. The mixture was cooled, poured into water (50 cm3) and extracted with 10% ethyl acetate-diethyl ether (2×50 cm3). The extracts were dried (MgSO4), filtered and concentrated to give a brown oil. Preparative thin layer chromatography on silica gel, eluting with 5% methanol-dichloromethane+1% ammonia, gave the title compound as a brown foam, which was crystallised as the oxalate salt from ethanol to give beige granules (0.007 g; 3%), m.p. 205°-210° C. (from EtOH); δH (360 MHz; d6 -DMSO+CF3CO2H) 2.54-2.70 (2H, m, NCH2CH2), 2.76 (2H, t, J 7.5, --CH2 --), 2.92 (2H, t, J 7.5, --CH2 --), 3.12-3.32 (1H, m, NCHAHBCH2), 3.60-3.78 (1H, m, NCHAHBCH2), 3.82-4.00 (2H, m, NCH2CH=C), 4.40 (2H, broad s, --CH2N), 5.90 (1H, s, NCH2 CH=C), 6.60 (1H, d, J 16.3, CH=CHPh), 6.96 (1H, d, J 16.3, CH=CHPh) 7.22-7.35 (6H, m, 6 of ArH), 7.49 (2H, d, J 7.4, 2 of ArH) and 7.64 (1H, d, J 6.6, 1 of ArH); m/z (CI+ ; NH3) 368 (MH+ ; 10%), 298 (10), 188 (15), 186 (20) and 184 (100). Found: M+ 367.2039. C25H25N3 requires 367.2048.

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 10% ethyl acetate-diethyl ether (2×50 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 gel, eluting with 5% methanol-dichloromethane+1% ammonia

Sources & evidence

ORD record
ord-974f68b382a64781826845bec4161d5c
Source dataset
uspto-grants-1997_11
Patent number
US05686480

Reaction notes

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