Trityl chloride → HCID 20267913, compound

HRID 1719217Notes

Reaction equation

HRID 1719217 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[C:10](Cl)([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:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl.CN(C)C>[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 6456Trityl chlorideHCID 76771-(2-Hydroxyethyl)piperazine

Product 1

HCID 20267913HCID 20267913, compoundYield 53.8%

Reagents, catalysts & solvents 2

HCID 1146TrimethylamineSolventHCID 6344DichloromethaneSolvent2×

Procedure

2.6 g of 1-(2-hydroxyethyl)piperazine was dissolved in a mixture of 20 ml of dry methylene chloride and 10 ml of trimethylamine and stirred at room temperature during the slow addition of a solution of 5.6 g of trityl chloride in 20 ml of dry methylene chloride. When the addition was complete, the solution was stirred for a further 18 hours at room temperature and then evaporated to dryness. Basification with 5% aqueous sodium bicarbonate solution and extraction with methylene chloride gave 4.0 g of 1-(2-hydroxyethyl)-4-triphenylmethylpiperazine, m.p. 82°, used directly in the next stage.

Workup

  1. additionWhen the addition
  2. customevaporated to dryness
  3. extractionBasification with 5% aqueous sodium bicarbonate solution and extraction with methylene chloride

Sources & evidence

ORD record
ord-3b64c2d4ad6f4d9e9ffb6c0ed9b94153
Source dataset
uspto-grants-1985_09
Patent number
US04539322

Reaction notes

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