Water → HCID 69637815, compound

HRID 1648367Notes

Reaction equation

HRID 1648367 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].C(=O)(O)[O-].[Na+].I[CH2:28][CH2:29][CH2:30][CH2:31][C:32]([NH:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:33].O>CN(C)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]([CH2:28][CH2:29][CH2:30][CH2:31][C:32](=[O:33])[NH:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:20][CH2:21]3)[C:9]=2[CH:8]=1)=[O:6])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium Bicarbonate2×HCID 19919599HCID 19919599, compoundHCID 19919629HCID 19919629, compound

Product 1

HCID 69637815HCID 69637815, compoundYield 6.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl-4-(1-piperazinyl)-benzo[b]thiophene-2-carboxylate monohydrochloride prepared in Example 5 (2.00 g, 6.12 mmol) in dry N,N-dimethylformamide (31 mL) was added sodium bicarbonate (1.03 g, 12.2 mmol) and 5-iodo-N-phenylpentanamide (1.86 g, 6.12 mmol). The mixture was heated at 80° C. under nitrogen for 24 h, cooled to 20° C., treated with saturated aqueous sodium bicarbonate (50 mL) and water (100 mL), and extracted with 2:1 ether:dichloromethane (4×75 mL). The combined extracts were diluted with ethanol (50 mL) washed with water (50 mL), brine (50 mL) dried over magnesium sulfate/sodium sulfate, filtered, and concentrated in vacuo. The crude product was chromatographed using 20:80 ethanol:ethyl acetate isolating the component with an Rf of ca. 0.5 (2.20 g). A solution of the product (0.20 g) in 5:2 ethanol:dichloromethane was treated with an equivalent of 1.0M hydrochloric acid and concentrated in vacuo. Recrystallization from 3:2 methanol:acetonitrile (10 mL) gave the title compound as a white solid (0.19 g).

Workup

  1. temperaturecooled to 20° C.
  2. extractionextracted with 2:1 ether
  3. additionThe combined extracts were diluted with ethanol (50 mL)
  4. washwashed with water (50 mL), brine (50 mL)
  5. dry with materialdried over magnesium sulfate/sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was chromatographed
  9. additionA solution of the product (0.20 g) in 5:2 ethanol:dichloromethane was treated with an equivalent of 1.0M hydrochloric acid
  10. concentrationconcentrated in vacuo
  11. customRecrystallization from 3:2 methanol

Sources & evidence

ORD record
ord-32f7e98c770b4b8fbadb45331b1bd58f
Source dataset
uspto-grants-1995_07
Patent number
US05436246

Reaction notes

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