HCID 15289966, compound → HCID 19919614, compound

HRID 1648362Notes

Reaction equation

HRID 1648362 reaction equation
C([O:3][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]([Cl:29])=[CH:25][CH:24]=4)[CH2:17][CH2:16]3)[C:8]=2[CH:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[ClH:29].[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][N:18]2[CH2:19][CH2:20][N:15]([C:14]3[C:8]4[CH:7]=[C:6]([CH2:4][OH:3])[S:10][C:9]=4[CH:11]=[CH:12][CH:13]=3)[CH2:16][CH2:17]2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 15289966HCID 15289966, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19919614HCID 19919614, compoundYield 150.1%

Procedure

In an analogous manner to example 2, the title compound (0.89 g) as a white solid, mp 248°-249° C. dec., is prepared from ethyl-4-[4-[2-(4-chlorophenyl)ethyl]-1-piperazinyl]-benzo[b]thiophene-2-carboxylate (1.20 g, 2.80 mmol, prepared in example 18) and lithium aluminum hydride (0.21 g, 5.6 mmol). The title compound is recrystallized from methanol (25 mL) and acetonitrile (10 mL); 1H NMR (CD3OD) δ 7.58 (1H, d, J=8.8 Hz), 7.37 (5H, m), 7.28 (1H, t, J=7.9 Hz), 7.00 (1H, d, J=7.8 Hz), 4.87 (2H, s), 4.07 (9H, m), 3.15 (3H, m); 13C NMR (CD3OD) δ 147.91, 147.51, 143.38, 136.81, 135.92, 134.81, 132.01, 130.62, 126.45, 119.92, 119.85, 114.46, 61.25, 59.20, 54.33, 51.01, 31.17; IR (KBr) 3319, 2584, 1462, 1446, 958, 779 cm-1 ; CI/MS 387(100%). IC50 =2 nM (5HT1ABinding Affinity) IC50 =10 nM (5HT1DBinding Affinity)

Sources & evidence

ORD record
ord-a00f9902ee374d3898ce1478da40c038
Source dataset
uspto-grants-1995_07
Patent number
US05436246

Reaction notes

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