Water → [4-(Spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methanol

HRID 390393Notes

Reaction equation

HRID 390393 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=1.O>CN(C=O)C>[N:1]1([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][OH:30])=[CH:25][CH:24]=2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 103304344-(Bromomethyl)benzyl alcoholHCID 156376162,3-Dihydrospiro(indene-1,4'-piperidine)

Product 1

HCID 67087241[4-(Spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methanolYield 109.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2,3-dihydrospiro[indene-1,4′-piperidine] (0.4 g, 1.78 mmol) in DMF (12 mL) is added Cs2CO3 (1.4 g, 4.4 mmol) and [4-(bromomethyl)phenyl]methanol (0.36 g, 1.78 mmol) and the reaction mixture is stirred overnight at room temperature. The reaction mixture is poured into cold water and extracted with EtOAc (3×50 mL). The combined organic layer is washed with brine solution, dried over Na2SO4, and concentrated under vacuum. The crude material is purified by silica gel chromatography (gradient DCM/MeOH 8/2) to give the title compound (0.6 g, 98%). ESI/MS m/z 308.40 (M+H)+.

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic layer is washed with brine solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe crude material is purified by silica gel chromatography (gradient DCM/MeOH 8/2)

Sources & evidence

ORD record
ord-6d6a5d797e17497aab8d4401c21b58ff
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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