Chlorodiphenylmethane → HCID 12151496, compound

HRID 1413944Notes

Reaction equation

HRID 1413944 reaction equation
Br[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.ClC(C1C=CC=CC=1)C1C=CC=CC=1.[NH:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[CH:2]([N:29]1[C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH2:31][CH2:30]1)([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

Participants

6

Reactant 4

HCID 7035ChlorodiphenylmethaneHCID 10328IndolineHCID 11430Potassium CarbonateHCID 236603Bromodiphenylmethane

Product 1

HCID 12151496HCID 12151496, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 49.4 g (0.2 mole) of bromodiphenylmethane (an equimolar quantity of chlorodiphenylmethane may be used instead), 23.8 g (0.2 mole) of indoline, 55.2 g (0.4 mole) of anhydrous potassium carbonate, and 200 ml of toluene is refluxed for 16 hrs under nitrogen with good stirring. The salts are removed by filtration, and the solvent is evaporated. The residue is chromatographed on silica gel with 30:70 toluene-hexane as the eluent. The product is a viscous oil, which can be crystallized from ethanol to give 1-benzhydryl-indoline, m.p. 62°-63.5°. The structure is confirmed by nmr spectroscopy and elemental analysis:

Workup

  1. temperatureis refluxed for 16 hrs under nitrogen with good stirring
  2. customThe salts are removed by filtration
  3. customthe solvent is evaporated
  4. customThe residue is chromatographed on silica gel with 30:70 toluene-hexane as the eluent
  5. customcan be crystallized from ethanol

Sources & evidence

ORD record
ord-406bd140ed194e379a66d94d7fffe542
Source dataset
uspto-grants-1981_02
Patent number
US04251659

Reaction notes

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