Epichlorohydrin → 1-[2-(4-Bromophenyl)-2-propyl]azetidin-3-ol

HRID 717105Notes

Reaction equation

HRID 717105 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH2:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl>CCO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:11]2[CH2:15][CH:14]([OH:16])[CH2:12]2)([CH3:9])[CH3:10])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 7835EpichlorohydrinHCID 230091162-(4-Bromophenyl)propan-2-amine

Product 1

HCID 898128241-[2-(4-Bromophenyl)-2-propyl]azetidin-3-olYield 38.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Bromophenyl)-1-methyl-ethylamine (1 g, 4.67 mmol) and epichlorohydrin (439 μl, 5.6 mmol) in EtOH (15 mL) were heated at 70° C. for 18 h. The reaction mixture was concentrated in vacuo and purified by reverse phase preparative HPLC-MS to obtain 1-[1-(4-bromo-phenyl)-1-methyl-ethyl]-azetidin-3-ol as a white solid (489 mg, 38%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by reverse phase preparative HPLC-MS

Sources & evidence

ORD record
ord-80d4f3e7eeb847a1a82650c798df9ac5
Source dataset
uspto-grants-2015_11
Patent number
US09193689B2

Reaction notes

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