Trityl chloride → (S)-4-N-Trityl-2-methyl-piperazine

HRID 1357602Notes

Reaction equation

HRID 1357602 reaction equation
[CH3:1][C@H:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>ClCCl>[CH3:1][C@@H:2]1[NH:3][CH2:4][CH2:5][N:6]([C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:7]1

Participants

4

Reactant 2

HCID 6456Trityl chlorideHCID 27342192-Methylpiperazine, (S)-

Product 1

HCID 7171814(S)-4-N-Trityl-2-methyl-piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(S)-methylpiperazine (2.62 g, 26.2 mmol) in dichloromethane (100 mL) was trityl chloride (7.30 g, 26.2 mmol) added and the mixture was stirred at ambient temperature for 1.5 h. The organic phase was washed (×1) with 1 M aqueous K2CO3, water, and brine. Drying (MgSO4) and solvent removal in vacuo furnished a quantitative yield of the title compound as a glassy oil which solidified upon standing. This material was used directly in the next step.

Workup

  1. additionadded
  2. washThe organic phase was washed (×1) with 1 M aqueous K2CO3, water, and brine
  3. customDrying
  4. custom(MgSO4) and solvent removal in vacuo

Sources & evidence

ORD record
ord-a2b2bf99fc22484e9207fbd9fbc7f6d2
Source dataset
uspto-grants-2003_07
Patent number
US06593330B2

Reaction notes

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