Ammonium Chloride → HCID 19919594, compound

HRID 1648365Notes

Reaction equation

HRID 1648365 reaction equation
C(O[C:4]([C:6]1[S:10][C:9]2[CH:11]=[CH:12][CH:13]=[C:14]([N:15]3[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)[CH2:17][CH2:16]3)[C:8]=2[CH:7]=1)=O)C.[Cl-:30].[NH4+:31].C[Al](C)C>C1(C)C=CC=CC=1>[ClH:30].[CH3:29][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][CH2:21][N:18]2[CH2:17][CH2:16][N:15]([C:14]3[C:8]4[CH:7]=[C:6]([C:4]#[N:31])[S:10][C:9]=4[CH:11]=[CH:12][CH:13]=3)[CH2:20][CH2:19]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 15289974HCID 15289974, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 19919594HCID 19919594, compoundYield 22.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In an analogous manner to example 3, the title compound (0.28 g) as a white solid, mp 260.5°-264.0° C., is prepared from ethyl-4-[4-[2-(4-methylphenyl)ethyl]-1-piperazinyl]-benzo[b]thiophene-2-carboxylate (1.30 g, 3.18 mmol, prepared in example 26), dry ammonium chloride ( 0.51 g, 9.6 mmol) and trimethyl aluminum (4.8 mL of a 2M solution in toluene, 9.6 mmol). The free base of the title compound is isolated by flash chromatography (ethyl acetate:hexane, 40:60 , TLC Rf =0.4); 1H NMR (DMSO-d6) δ11.48 (1H, bs), 8.51 (1H, s), 7.82 (1H, d, J=8.2 Hz), 7.56 (1H, t, J=7.9 Hz), 7.19 (4H, m), 7.10 (1H, d, J=7.6 Hz), 3.65 (4H, m), 3.45 (6 H, m), 3.11 (2H, m), 2.29 (3H, s),; 13C NMR (DMSO-d6) δ148.03, 142.47, 135.82, 134.78, 133.93, 131.41, 129.17, 128.52, 117.51, 114.72, 113.96, 107.09, 56.20, 51.03, 48.47, 28.83, 20.59; IR (KBr) 2539, 2448, 1564, 1458, 959 cm-1 ; CI/MS (CH4) 362(100%).

Sources & evidence

ORD record
ord-f8a64048c6f44f06bd6ecdd97867e4e4
Source dataset
uspto-grants-1995_07
Patent number
US05436246

Reaction notes

Loading…