Benzene → HCID 21561539, compound

HRID 1581124Notes

Reaction equation

HRID 1581124 reaction equation
[C:1]1([CH:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:8][CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]1([CH:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:24][CH2:25][Cl:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1C=CC=CC=1>C1(C)C(C)=CC=CC=1>[ClH:26].[C:11]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:8][CH2:9][NH:10][CH2:25][CH2:24][CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 796983,3-DiphenylpropylamineHCID 1901351,1'-(3-Chloropropane-1,1-diyl)dibenzene

Product 1

HCID 21561539HCID 21561539, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 3,3-diphenylpropylamine (4.9 g) and 3,3-diphenyl-1-chloropropane (5.0 g) in xylene (10 ml) was heated at 120° to 130°C for 4 hours. After cooling, a small amount of benzene was added to the reaction mixture and then the mixture was filtered to remove 3,3-diphenylpropylamine hydrochloride. The filtrate was washed with 5 % hydrochloric acid and water in order. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The resulting crystalline residue was recrystallized from methanol to give bis(3,3-diphenylpropyl)amine hydrochloride (3.0 g.). M.P. 192° to 194°C.

Workup

  1. temperaturewas heated at 120° to 130°C for 4 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. customto remove 3,3-diphenylpropylamine hydrochloride
  5. washThe filtrate was washed with 5 % hydrochloric acid and water in order
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customevaporated under reduced pressure
  8. customThe resulting crystalline residue was recrystallized from methanol

Sources & evidence

ORD record
ord-16ad1a4df9564134a505e43f7b4d7e5a
Source dataset
uspto-grants-1976_01
Patent number
US03935268

Reaction notes

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