Trityl chloride → HCID 10088037, compound

HRID 1063856Notes

Reaction equation

HRID 1063856 reaction equation
[NH2:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4].C(N(CC)CC)C.[C:14]1([C:20](Cl)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>ClCCl>[C:14]1([C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:1][CH2:2][C:3]([NH2:6])([CH3:5])[CH3:4])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 131282-Methylpropylenediamine

Product 1

HCID 10088037HCID 10088037, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10 mL (95.4 mMol) 1,2-diamino-2-methylpropane and 20 mL (144 mMol) triethylamine in 300 mL dichloromethane was cooled to 0° C. To this solution was added a solution of 26 gm (93.3 mMol) (triphenyl)methyl chloride in 50 mL dichloromethane. The resulting mixture was stirred at room temperature for about 18 hours. The reaction mixture was washed with saturated aqueous sodium bicarbonate, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with ethyl acetate containing from 0–10% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 16.0 gm (52%) of the desired compound as a white solid.

Workup

  1. washThe reaction mixture was washed with saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. washeluting with ethyl acetate containing from 0–10% methanol
  5. additionFractions containing product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-29e680e57a3747c18f7d6e14eac7ea8d
Source dataset
uspto-grants-2005_11
Patent number
US06967201B1

Reaction notes

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