Boron tribromide → N-Desmethylmeptazinol

HRID 1594860Notes

Reaction equation

HRID 1594860 reaction equation
B(Br)(Br)Br.[CH2:5]([C:7]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21]C)[CH:16]=2)[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][C:8]1=O)[CH3:6]>C(Cl)Cl>[CH2:5]([C:7]1([C:15]2[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=2)[CH2:13][CH2:12][CH2:11][CH2:10][NH:9][CH2:8]1)[CH3:6]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 28154553-Ethyl-3-(3-methoxyphenyl)azepan-2-one

Product 1

HCID 6453793N-Desmethylmeptazinol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 1M solution of BBr3(2.56 mL, 2.56 mmol) in CH2Cl2 was added to 3-ethyl-3-(3-methoxy-phenyl)-azepane (as described in Example 8, Step A) (0.300 g, 0.1.28 mmol) dissolved in anhydrous CH2Cl2 (10 mL) at −78° C. After 20 h of stirring at room temperature, the reaction was quenched with sat. NaHCO3 solution, extracted with CH2Cl2 (3×), dried (MgSO4) and concentrated to give the title compound.

Workup

  1. customthe reaction was quenched with sat. NaHCO3 solution
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7a97e24925f84994b98c8bb60532b1f9
Source dataset
uspto-grants-2001_09
Patent number
US06284755B1

Reaction notes

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