Trityl chloride → HCID 19004143, compound

HRID 2226046Notes

Reaction equation

HRID 2226046 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[CH2:9][NH:8][CH2:7][CH2:6][NH:5]1.[C:10]1([C:16](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N([CH2:35][CH3:36])CC)C>C(Cl)Cl>[C:16]([O:1][CH2:2][CH2:3][CH:4]1[CH2:9][N:8]([C:16]([C:36]2[CH:35]=[CH:28][CH:23]=[CH:24][CH:25]=2)([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:7][CH2:6][NH:5]1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 91308Piperazineethanol

Product 1

HCID 19004143HCID 19004143, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 255 mg (1.96 mmol) of (±) 2-(2-hydroxyethyl)piperazine and 1.25 g (4.50 mmol) of triphenylmethyl chloride in 5.0 ml of methylene chloride was added 550 ml (3.95 mmol) of triethylamine in one portion and the mixture was stirred at room temperature overnight under a nitrogen atmosphere. The reaction was diluted with 5 mL of methylene chloride and washed with water (3×5 ml) and the layers separated. The aqueous layer was extracted with 10 mL of methylene chloride. The organic layers were combined and washed with 15 mL of saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to an orange foam. Flash chromatography on 75 g of silica gel using a gradient elution of 1:9 v/v ethyl acetate/hexane to 1:9 v/v ethanol/ethyl acetate yielded 401 mg (33%) of a foam.

Workup

  1. washwashed with water (3×5 ml)
  2. customthe layers separated
  3. extractionThe aqueous layer was extracted with 10 mL of methylene chloride
  4. washwashed with 15 mL of saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo to an orange foam
  8. washFlash chromatography on 75 g of silica gel using a gradient elution of 1:9 v/v ethyl acetate/hexane to 1:9 v/v ethanol/ethyl acetate

Sources & evidence

ORD record
ord-4b3a227fe2f740118f4861dd8b81ac7c
Source dataset
uspto-grants-1994_09
Patent number
US05344830

Reaction notes

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