Water → HCID 178420098, compound

HRID 2293519Notes

Reaction equation

HRID 2293519 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]2[CH2:31]CNC[CH2:27]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]2[CH2:31][CH2:18][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)[CH2:19][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 698734-PhenylpiperidineHCID 81531DiisopropylethylamineHCID 178483382HCID 178483382, compound

Product 1

HCID 178420098HCID 178420098, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4,5-dihydro-1H-benzo[g]indazol-3-ylmethyl)-trimethylammonium iodide (0.30 g), 4-phenylpiperidine (0.15 g) and diisopropylethylamine (0.30 cm3) in DMF (10 cm3) was heated under argon at 80° C. for 24 hours. The mixture was cooled, poured into water (25 cm3) and extracted with 50% ethyl acetate-diethyl ether (2×25 cm3). The extracts were dried (MgSO4), filtered and concentrated to give the title compound as a brown oil. This was crystallised as the half-oxalate salt from DMF-ethanol-ethyl acetate (0.045 g; 12%), m.p. 128°-230° C. (from DMF-EtOH-EtOAc); Found: C, 73.85; H, 6.8; N, 10.8. C23H25N3.0.5(CO2H)2.0.1(H2O) requires C, 73.9; H, 6.8; N, 10.8%. δH (360 MHz; d6 -DMSO; 353K) 1.70-1.92 (4H, m, 2 x NCH2CH2), 2.40-2.56 (2H, m, 2 x NCHAHBCH2 ; partially obscured by DMSO peak), 2.58-2.64 (1H, m, NCH2CH2CH), 2.78 (2H, t, J 7.5, --CH2 --), 2.90 (2H, t, J 7.5, --CH2 --), 3.16 (2H, broad d, J 11, 2 x NCHA HBCH2), 3.82 (2H, s, --CH2N), 7.15-7.30 (8H, m, 8 of ArH) and 7.66 (1H, d, J 7.7, 1 of ArH); m/z (CI+ ; NH3) 344 (MH+ ; 5%), 235 (5), 185 (18) and 162 (100).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 50% ethyl acetate-diethyl ether (2×25 cm3)
  3. dry with materialThe extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-747e4c88f3604563a278c221f7a190c3
Source dataset
uspto-grants-1997_11
Patent number
US05686480

Reaction notes

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