Ethanolamine → 2-((Triphenylmethyl)amino)ethanol

HRID 1755768Notes

Reaction equation

HRID 1755768 reaction equation
C(NCC)C.[CH2:6]([CH2:8][NH2:9])[OH:7].[C:10]1([C:16]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)Cl)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C(O)(C)C>[C:16]([NH:9][CH2:8][CH2:6][OH:7])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 6456Trityl chlorideHCID 8021Diethylamine

Product 1

HCID 31256082-((Triphenylmethyl)amino)ethanolYield 85.7%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of isopropanol (750 ml), diethylamine (75 ml), ethanolamine (98%, 62.3 g, 1 mole) and triphenylchloromethane (97%, 143.7 g, 0.50 moles) was stirred at room temperature for 3 hours. The resulting solution was then poured into ice-cold water (4 l) under continuous stirring and the resulting precipitate was filtered off and dried. The crude product was digested in toluene (340 ml), then filtered off and dried in vacuo at 60° C. Thus 130 g (85%) of the pure desired compound were obtained.

Workup

  1. stirringunder continuous stirring
  2. filtrationthe resulting precipitate was filtered off
  3. customdried
  4. filtrationfiltered off
  5. customdried in vacuo at 60° C

Sources & evidence

ORD record
ord-7f2c441a72e544e2982cd0e69bd5ec83
Source dataset
uspto-grants-1995_08
Patent number
US05438145

Reaction notes

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