Chlorodiphenylmethane → HCID 58911304, compound

HRID 1295872Notes

Reaction equation

HRID 1295872 reaction equation
Cl[CH:2]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CN[CH2:17][CH:18]1[CH2:22][CH2:21][NH:20][CH2:19]1.[C:23]([O:27][C:28](=[O:30])[NH2:29])([CH3:26])([CH3:25])[CH3:24].[C:31]([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[C:23]([O:27][C:28](=[O:30])[N:29]([CH2:17][CH:18]1[CH2:22][CH2:21][N:20]([CH:2]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:19]1)[CH3:31])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 7035ChlorodiphenylmethaneHCID 11430Potassium CarbonateHCID 77922tert-Butyl carbamateHCID 13491795N-Methyl-1-(pyrrolidin-3-yl)methanamine

Product 1

HCID 58911304HCID 58911304, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a solution of chlorodiphenylmethane (0.79 g, 3.22 mmol) in butanone (20 ml) was added methyl-pyrrolidine-3-ylmethyl-amine)-carbamic acid tert-butyl ester (0.69 g, 3.22 mmol), K2CO3 (0.54 g, 3.8 mmol) and KI (0.54 g, 3.22 mmol). The mixture was heated under reflux for 18 hours, then filtered and the solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (50 ml) and washed with water (10 ml). Drying over MgSO4 and removal of solvent under reduced pressure followed by column chromatography using CH2Cl2:CH3OH (20:1) gives the desired product in 75% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in CH2Cl2 (50 ml)
  6. washwashed with water (10 ml)
  7. dry with materialDrying over MgSO4 and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-01a5fbbba8394b49b6256cf0d60d32ed
Source dataset
uspto-grants-2007_07
Patent number
US07244758B2

Reaction notes

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