Phenol → HCID 12150158, compound

HRID 1827281Notes

Reaction equation

HRID 1827281 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[CH2:6][N:7]1[CH2:23][CH2:22][C:10]2([N:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:13][NH:12][C:11]2=[O:21])[CH2:9][CH2:8]1.[C:27]1([OH:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:27]1([O:33][CH2:2][C:3]2[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=2)[CH2:6][N:7]2[CH2:23][CH2:22][C:10]3([N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)[CH2:13][NH:12][C:11]3=[O:21])[CH2:9][CH2:8]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 12150172HCID 12150172, compound

Product 1

HCID 12150158HCID 12150158, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-(3-chloromethyl-benzyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4one, prepared as in Example 8 above, (203 mg, 0.500 mmol), phenol (56.8 mg, 0.603 mmol), KI (83.1 mg, 0.500 mmol) and K2CO3 (174 mg, 1.26 mmol) in DMF was stirred at room temperature for 1 day. The reaction mixture was diluted with H2O and a white solid precipitated. The solid was collected by filtration, washed with H2O and dried under house vacuum. The crude product was initially purified by flash chromatography (5% MeOH in CHCl3) and by tapered prep TLC (5% MeOH in CHCl3) to yield the title product as a white amorphous solid.

Workup

  1. customa white solid precipitated
  2. filtrationThe solid was collected by filtration
  3. washwashed with H2O
  4. customdried under house vacuum
  5. customThe crude product was initially purified by flash chromatography (5% MeOH in CHCl3)

Sources & evidence

ORD record
ord-7b67371e0659408fac4434ffa72438e2
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

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