1-(2-Bromoethyl)-4-chlorobenzene → HCID 67620121, compound

HRID 1648361Notes

Reaction equation

HRID 1648361 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([N:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[C:9]=2[CH:8]=1)=[O:6])[CH3:3].[Cl:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Br)=[CH:25][CH:24]=1.C(=O)(O)[O-].[Na+]>CS(C)=O>[ClH:22].[CH2:2]([O:4][C:5]([C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[C:15]([N:16]3[CH2:17][CH2:18][N:19]([CH2:28][CH2:27][C:26]4[CH:30]=[CH:31][C:23]([Cl:22])=[CH:24][CH:25]=4)[CH2:20][CH2:21]3)[C:9]=2[CH:8]=1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 230291-(2-Bromoethyl)-4-chlorobenzeneHCID 516892Sodium BicarbonateHCID 19919599HCID 19919599, compound

Product 1

HCID 67620121HCID 67620121, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In an analogous manner to example 6, the title compound (0.56 g) as a white solid, mp 263°-266° C. dec. is prepared from ethyl-4-(1-piperazinyl)benzo[b]thiophene-2-carboxylate monohydrochloride (4.63 g, 14.2 mmol, prepared in example 5), 4-chlorophenethyl bromide (3.27 g, 14.9 mmol), sodium bicarbonate (2.44 g, 29.1 mmol) and anhydrous dimethyl sulfoxide (75 mL). The title compound is recrystallized from methanol (35 mL) and acetonitrile (35 mL); 1H NMR (DMSO-d6) δ 10.76 (1H, s), 8.10 (1H, s), 7.77 (1H, d, J=8.0 Hz), 7.44 (5H, m), 7.08 (1H, d, J=7.8 Hz), 4.37 (2H, q, J=7.0 Hz), 3.64 (4H, m), 3.56 (8H, m), 3.13 (2H, m), 1.34 (3 H, t, J=7.1 Hz); 13C NMR (DMSO-d6) δ 162.42, 151.71, 143.15, 132.82, 130.94, 128.95, 128.86, 128.63, 128.34, 117.59, 113.66, 113.59, 61.97, 52.66, 51.40, 31.20, 24.06, 14.47; IR (KBr) 1714, 1448, 1282, 1246, 754 cm-1 ; CI/MS (CH4) 429(100%). IC50 =53 nM (5HT1ABinding Affinity) IC50 =411 nM (5HT1DBinding Affinity) pA2 =6.51 (blocking of 5-HTl-like-mediated contraction in canine saphenous vein)

Workup

  1. customThe title compound is recrystallized from methanol (35 mL) and acetonitrile (35 mL)

Sources & evidence

ORD record
ord-6d33db5fab9d48f1b402861e1c56adfc
Source dataset
uspto-grants-1995_07
Patent number
US05436246

Reaction notes

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