(3-Bromopropyl)benzene → HCID 67619730, compound

HRID 1648359Notes

Reaction equation

HRID 1648359 reaction equation
[ClH:1].[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].Br[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(=O)(O)[O-].[Na+]>CS(C)=O>[ClH:1].[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]([CH2:23][CH2:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:20][CH2:21]3)[C:9]=2[CH:8]=1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 12503(3-Bromopropyl)benzeneHCID 516892Sodium BicarbonateHCID 19919599HCID 19919599, compound

Product 1

HCID 67619730HCID 67619730, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In an analogous manner to example 6, the title compound (0.99 g) as a tan solid, mp 210.5°-213° C., is prepared from ethyl-4-(1-piperazinyl)-benzo[b]thiophene-2-carboxylate monohydrochloride (2.40 g, 8.27 mmol, prepared in example 5), dry dimethyl sulfoxide (45 mL), 1-bromo-3-phenylpropane (1.20 mL, 8.27 mmol) and sodium bicarbonate (0.69 g, 8.27 mmol). Recrystallize the title compound from warm methanol (10 mL); 1H NMR (DMSO-d6) δ 11.05 (bs), 7.76 (1H, d, J=8.2 Hz), 7.49 (1H, t, J=7.9 Hz), 7.28 (5H, m), 7.06 (1H, d, J=7.6 Hz), 4.37 (2H, q, J=7.2 Hz) 3.62 (2H, bd), 3.53 (2H, bd), 3.32 (4H, m), 3.18 (2H, m), 2.69 (2H, m), 1.34 (3H, t, J=7.1 Hz); 13C NMR (DMSO-d6) δ 161.86, 148.25, 142.82, 140.49, 132.62, 131.96, 128.41, 128.33, 128.23, 127.86, 126.11, 117.96, 113.65, 61.49, 55.24, 51.03, 48.76, 32.07, 24.71, 14.16; IR (KBr) 2970, 1709, 1284, 1258 cm-1 ; CI/MS (CH4) 409(100%), 408(75%). IC50 =239 nM (5HT1ABinding Affinity) IC50 =551 nM (5HT1DBinding Affinity)

Sources & evidence

ORD record
ord-50a0d68bbab4480a8b1f5b91d0c10c5c
Source dataset
uspto-grants-1995_07
Patent number
US05436246

Reaction notes

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