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

HRID 497560Notes

Reaction equation

HRID 497560 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][OH:5].Cl[C:7]([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:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>ClCCl.O>[OH:5][CH2:4][CH2:3][CH2:2][NH:1][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 90863-Amino-1-propanol

Product 1

HCID 31113793-(Tritylamino)propan-1-olYield 66%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-amino-1-propanol (51 ml, 0.66 mol), chlorotriphenylmethane (184 g, 0.66 mol) and triethylamine (92 ml, 0.66 mol) in dichloromethane (1000 ml) was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and the layers separated. The aqueous phase was extracted with further dichloromethane (2×) and the combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was triturated well with diisopropyl ether, and the resulting solid was filtered and dried. This solid was then triturated with methanol, the suspension filtered, and the filtrate concentrated under reduced pressure, to give the title compound as a white solid, 139.1 g, 66% yield.

Workup

  1. customthe layers separated
  2. extractionThe aqueous phase was extracted with further dichloromethane (2×)
  3. dry with materialthe combined organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated well with diisopropyl ether
  7. filtrationthe resulting solid was filtered
  8. customdried
  9. customThis solid was then triturated with methanol
  10. filtrationthe suspension filtered
  11. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8e61725cb96947129c14bb6d737a2cd6
Source dataset
uspto-grants-2005_09
Patent number
US06949577B2

Reaction notes

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