Cesium carbonate → HCID 57586394, compound

HRID 2190329Notes

Reaction equation

HRID 2190329 reaction equation
Br[CH2:2][CH2:3][CH:4]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:17]1([NH2:20])[CH2:19][CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O>[C:5]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3][CH2:2][NH:20][CH:17]2[CH2:19][CH2:18]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 69828CyclopropylamineHCID 883331,1'-(3-Bromopropylidene)bisbenzene

Product 1

HCID 57586394HCID 57586394, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-bromo-1,1-diphenylpropane 9 (2.06 g, 7.49 mmol) in DMF (15 mL) at room temperature was added cyclopropylamine (3.26 g, 57.1 mmol, 4.0 mL) and cesium carbonate (3.19 g, 9.79 mmol). The reaction mixture was stirred at room temperature for 20 h and diluted with EtOAc. The aqueous phase was extracted with EtOAc (2×) and the combined organic extracts were washed with brine (1×), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 1% to 6% MeOH (2 M NH3) in DCM) gave N-(3,3-diphenylpropyl)cyclopropanamine 10 as a colorless oil. Mass spectrum: calculated for C18H21N 251.2; found 252.2 (M++1).

Workup

  1. extractionThe aqueous phase was extracted with EtOAc (2×)
  2. washthe combined organic extracts were washed with brine (1×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash column chromatography on silica gel (eluted with 1% to 6% MeOH (2 M NH3) in DCM)

Sources & evidence

ORD record
ord-51e9f4cf3c9f49dfa3348c34db6ac49a
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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