3-Bromo-1-propanol → 4-Benzhydryl-1-piperazinepropanol

HRID 366421Notes

Reaction equation

HRID 366421 reaction equation
[CH:1]([N:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.Br[CH2:30][CH2:31][CH2:32][OH:33]>O1CCOCC1.O>[CH:1]([N:14]1[CH2:19][CH2:18][N:17]([CH2:30][CH2:31][CH2:32][OH:33])[CH2:16][CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 123083-Bromo-1-propanolHCID 70048BenzhydrylpiperazineHCID 81531Diisopropylethylamine

Product 1

HCID 155241464-Benzhydryl-1-piperazinepropanol

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To 1-benzhydrylpiperazine (64 mmol) and diisopropylethylamine (77 mmol) in dioxane/H2O (9:1, 100 mL) is added 3-bromo-1-propanol (64 mmol) while stirring. After about 17 hours, the solution is concentrated in vacuo, and the residue is taken up in EtOAc (250 mL) and washed with 1N NaOH (2×100 mL), and brine (2×). The organic phase is dried over Na2SO4 (s), concentrated in vacuo and recrystallized from hot EtOAc to afford white crystalline product.

Workup

  1. concentrationthe solution is concentrated in vacuo
  2. washwashed with 1N NaOH (2×100 mL), and brine (2×)
  3. dry with materialThe organic phase is dried over Na2SO4 (s)
  4. concentrationconcentrated in vacuo
  5. customrecrystallized from hot EtOAc
  6. customto afford white crystalline product

Sources & evidence

ORD record
ord-b0a72097869f4f86abbce74ae5ed7951
Source dataset
uspto-grants-2000_10
Patent number
US06130217

Reaction notes

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