Sodium Chloride → HCID 53645033, compound

HRID 1387009Notes

Reaction equation

HRID 1387009 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:12]([C:13](=[O:29])[C:14]3[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][N:23]4[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]4)=[CH:16][CH:15]=3)=[C:11]([C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)[S:10][C:9]=2[CH:37]=1)=[O:4].Cl.Cl[CH2:40][CH2:41][N:42]1[CH2:46][CH2:45][CH2:44][CH2:43]1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CN(C=O)C.C1COCC1.O>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[C:12]([C:13](=[O:29])[C:14]3[CH:15]=[CH:16][C:17]([O:20][CH2:21][CH2:22][N:23]4[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]4)=[CH:18][CH:19]=3)=[C:11]([C:30]3[CH:31]=[CH:32][C:33]([O:36][CH2:40][CH2:41][N:42]4[CH2:46][CH2:45][CH2:44][CH2:43]4)=[CH:34][CH:35]=3)[S:10][C:9]=2[CH:37]=1)=[O:4]

Participants

8

Reactant 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 10791955HCID 10791955, compound

Product 1

HCID 53645033HCID 53645033, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.5 g (2.9 mmol) of 2-(4-hydroxyphenyl)-3-[4-[2-(1-piperidinyl)ethoxy]benzoyl]benzo[b]thiophene-6-carboxylic acid methyl ester (Part C) and 544 mg (3.2 mmol) of 1-(2-chloroethyl)pyrrolidine hydrochloride in 20 mL of anhydrous DMF was added 2.37 g (7.3 mmol) of cesium carbonate at room temperature under a nitrogen atmosphere. The reaction mixture was heated at 60° C. for 4 h and then cooled to room temperature and diluted with 125 mL of THF and 75 mL of water. The aqueous layer was saturated with sodium chloride and extracted twice with 50 mL portions of THF. The combined organic layers were washed with brine, dried with anhydrous sodium sulfate, and concentrated at reduced pressure. The residue was purified on silica gel (1:1 MeOH/TEA (10%) in THF) to give 1.26 g (2.2 mmol, 77%) of an orange-brown foam.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted twice with 50 mL portions of THF
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was purified on silica gel (1:1 MeOH/TEA (10%) in THF)

Sources & evidence

ORD record
ord-4dc4262d7079496abd9ba08c0d437947
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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