Water → HCID 19919567, compound

HRID 1648366Notes

Reaction equation

HRID 1648366 reaction equation
[ClH:1].[CH2:2]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:24]3[CH:23]=[C:22]([C:25](=[O:27])[CH3:26])[S:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[BH4-].[Na+].O>CO>[ClH:1].[CH2:2]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[C:24]3[CH:23]=[C:22]([CH:25]([OH:27])[CH3:26])[S:21][C:20]=3[CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 19919558HCID 19919558, compound

Product 1

HCID 19919567HCID 19919567, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To partially dissolved 1-[4-(4-phenethyl-piperazin-1-yl)benzo[b]thiophen-2-yl]-ethanone hydrochloride (0.92 g, 2.5 mmol, product from Example 42) in methanol (70 mL) is added sodium borohydride (0.19 g, 5.0 mmol). After 0.33 h, the reaction is clear and homogeneous. The reaction is worked up after 2 h by pouring into water (10 mL), extracting with dichloromethane (3×75 mL), and concentrating the sodium sulfate dried extracts in vacuo. The product (Rf of 0.3 in ethyl acetate) is dissolved in acetonitrile (50 mL), treated with 1.0M hydrochloric acid (2.5 mL), concentrated in vacuo, then reconcentrated from acetonitrile:methanol to give a white solid. After vacuum drying for 9 h at 70° C., the title compound is isolated as a white solid (0.865 g). 1H NMR (d6 -DMSO): 11.48 (1H, bs), 7.61 (1H, d, J=8.0 Hz), 7.40-7.23 (7H), 6.95 (1H, d, J=7.6 Hz), 5.76 (1H, bs), 5.07 (1H, q, J=6.2 Hz), 3.69 (2H, bd, J=10.6 Hz), 3.53 (2H, m), 3.45-3.25(6H), 3.17 (2H, m), 1.50 (3H, d, J=6.4 Hz) ppm. 13C NMR (d6 -DMSO): 152.13, 146.05, 139.74, 137.10, 133.35, 128.67, 126.79, 124.47, 117.62, 116.20, 112.54, 64.86, 56.19, 51.18, 48.45, 48.24, 29.29, 25.68 ppm. IR (KBr): 3351, 2575, 2554, 2446, 1570 cm-1. CIMS (methane): 367 (92%), 349 (100%), 275 (82% ).

Workup

  1. waitThe reaction is worked up after 2 h
  2. extractionextracting with dichloromethane (3×75 mL)
  3. concentrationconcentrating the sodium sulfate dried extracts in vacuo
  4. dissolutionThe product (Rf of 0.3 in ethyl acetate) is dissolved in acetonitrile (50 mL)
  5. additiontreated with 1.0M hydrochloric acid (2.5 mL)
  6. concentrationconcentrated in vacuo
  7. custommethanol to give a white solid
  8. customAfter vacuum drying for 9 h at 70° C.

Sources & evidence

ORD record
ord-2d79a9139a534f72a559ab377ba7f7a8
Source dataset
uspto-grants-1995_07
Patent number
US05436246

Reaction notes

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