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Dimethylformamide → 3-Phenyl-2-[4-[3-(1-pyrrolidinyl)propoxy]phenyl]-1,4-benzoxathiin

HRID 1696685
Notes
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Reaction equation

HRID 1696685 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br.BrC[CH2:10][CH2:11][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.CN(C=O)C.[C:23]1([C:29]2[S:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[O:31][C:30]=2[C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(OCC)(=O)C>[C:23]1([C:29]2[S:34][C:33]3[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=3[O:31][C:30]=2[C:39]2[CH:40]=[CH:41][C:42]([O:45][CH2:15][CH2:16][CH2:17][N:12]3[CH2:11][CH2:10][CH2:14][CH2:13]3)=[CH:43][CH:44]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 201357721-(3-Bromopropyl)piperidine HydrobromideHCID 593967364-(3-Phenyl-1,4-benzoxathiin-2-yl)phenol

Product 1

HCID 593967663-Phenyl-2-[4-[3-(1-pyrrolidinyl)propoxy]phenyl]-1,4-benzoxathiinYield 53.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

Potassium carbonate (83 mg) and 1-(3-bromopropyl)piperidine hydrobromide (54.6 mg) were added to a DMF (3 mL) solution of 4-(3-phenyl-1,4-benzoxathiin-2-yl)phenol (63.7 mg, 0.2 mmol) obtained in Reference Example 1-1, and stirred at 80° C. for 8 hours. The reaction liquid was restored to room temperature, diluted with ethyl acetate, and extracted with distilled water. The organic layer was dried with magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by preparative thin-layer silica gel column chromatography (chloroform:methanol=9:1) to obtain the entitled compound (43.7 mg, 51%) as a yellow oil.

Workup

  1. customobtained in Reference Example 1-1
  2. customThe reaction liquid
  3. customwas restored to room temperature
  4. extractionextracted with distilled water
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by preparative thin-layer silica gel column chromatography (chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-faf5a1f3c14d4aeaabe3000da1f38c21
Source dataset
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08163770B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes