Bromodiphenylmethane → HCID 19004205, compound

HRID 2225441Notes

Reaction equation

HRID 2225441 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][O:14][CH:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 236603BromodiphenylmethaneHCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

Product 1

HCID 19004205HCID 19004205, compoundYield 48.8%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-benzylpyrrolidine-3-methanol (1.72 g) (J. Org. Chem., 1961, 26, 1521) and bromodiphenylmethane (4.94 g) in xylene (150 ml) was heated under reflux for 3 hours, allowed to cool to room temperature, diluted with ethyl acetate, washed with 10% aqueous sodium carbonate solution, dried over magnesium sulphate and evaporated. The residue was purified by chromatography on silica using dichloromethane plus 20% ethyl acetate plus 0-10% methanol as eluant. Appropriate fractions were combined and evaporated to give the title compound (1.57 g) as a pale brown oil which was charcterised by its 1H-NMR spectrum.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. washwashed with 10% aqueous sodium carbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was purified by chromatography on silica
  7. customevaporated

Sources & evidence

ORD record
ord-dd961cf4be9543c1a518c32d9450d069
Source dataset
uspto-grants-1994_09
Patent number
US05344835

Reaction notes

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