Trityl chloride → 3-(Tritylamino)propan-1-ol

HRID 481002Notes

Reaction equation

HRID 481002 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].[C:6](Cl)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1COCC1>[C:6]([NH:1][CH2:2][CH2:3][CH2:4][OH:5])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 90863-Amino-1-propanol

Product 1

HCID 31113793-(Tritylamino)propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3-(Tritylamino)-1-propanol was prepared according to the literature procedure (J.Heterocycl.Chem.; 1993, 30, 1197). To a solution of 3-amino-1-propanol (15.0 g/200 mmol) in THF (100 ml) was added a solution of tritylchloride (23.2 g/83.3 mmol) in THF (100 ml) dropwise at 0° C., and then the resulting solution was stirred at room temperature for 4 days. The solution was evaporated. The resulting residue was dissolved in water (100 ml) and dichloromethane (100 ml). The organic layer was separated. The aqueous layer was extracted with dichloromethane (100 ml×2). The combined organic layer was washed with brine (30 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified by recrystallization from toluene/hexane to afford a white crystal. (21.0 g/80%).

Workup

  1. customThe solution was evaporated
  2. dissolutionThe resulting residue was dissolved in water (100 ml)
  3. customThe organic layer was separated
  4. extractionThe aqueous layer was extracted with dichloromethane (100 ml×2)
  5. washThe combined organic layer was washed with brine (30 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by recrystallization from toluene/hexane
  10. customto afford a white crystal

Sources & evidence

ORD record
ord-b98749b21d3a4d08890040fbad05b6c1
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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