Water → HCID 68183338, compound

HRID 1615478Notes

Reaction equation

HRID 1615478 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]3[CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[S:17][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.O.C(OCC)(=O)C>[OH-].[Na+]>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]3[CH:15]=[C:16]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)[S:17][C:13]=3[CH2:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 68183340HCID 68183340, compound

Product 1

HCID 68183338HCID 68183338, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

In a 250 mL round bottomed flask was placed 4-[4-(4-chlorophenyl)-4,5,6,7-tetrahydro-1-benzothien-2-yl]pyridine hydrochloride (2.1 g, 5.8 mmol) and then suspended in 1 M of Sodium hydroxide in water (50 mL, 50 mmol). To the mixture was added ethyl acetate (50 mL) and the mixture was vigorously stirred for 30 min at rt. The aqueous phase was extracted with EtOAc (50 mL×2) and the combined organic phase was dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure to obtain the title compound (1.85 g; 98%) as a brown syrup, which was spontaneously solidified by keeping on standing at rt for 3 h. 1H NMR (300 MHz, d1-chloroform) δ: 8.51 (d, 2H), 7.26-7.35 (m, 4H), 7.09 (d, 2H), 6.91 (s, 1H), 3.98 (t, 1H), 2.90 (t, 2H), 1.71-2.21 (m, 6H).

Workup

  1. customIn a 250 mL round bottomed flask was placed
  2. extractionThe aqueous phase was extracted with EtOAc (50 mL×2)
  3. dry with materialthe combined organic phase was dried over anhydrous MgSO4
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-13d1ba4adbc04156b2693130d0e01f1c
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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