Trityl chloride → 2-((Triphenylmethyl)amino)ethanol

HRID 863837Notes

Reaction equation

HRID 863837 reaction equation
Cl.[CH2:2]([CH2:4][NH2:5])[OH:3].CCN(CC)CC.[C:13](Cl)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl.CC#N.C(Cl)Cl>[C:13]([NH:5][CH2:4][CH2:2][OH:3])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 74819Ethanolamine Hydrochloride

Product 1

HCID 31256082-((Triphenylmethyl)amino)ethanol

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21877088Acetonitrile methylene chlorideSolvent

Procedure

Ethanolamine hydrochloride (9.9 g; 100 mmol) is partially dissolved in CH2Cl2 /CH3CN (200 ml/100 ml) and Et3N (23 ml; 170 mmol) is then added. Tritylchloride (18.9 g; 67.6 mmol) is added portionwise over 30 minutes. After the addition is complete the reaction mixture is allowed to stir an additional 30 minutes, diluted with CH2Cl2, washed With H2O 2× and brine, dried (MgSO4), concentrated in vacuo and purified by column chromatography with silica/CH2Cl2 to give N-tritylethanolamine as an oil which is used directly in Step B.

Workup

  1. additionAfter the addition
  2. washwashed With H2O 2× and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography with silica/CH2Cl2

Sources & evidence

ORD record
ord-f8badbd1babf45b68573c66678a09b47
Source dataset
uspto-grants-1996_10
Patent number
US05561143

Reaction notes

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