Ammonia → 2,3,4,5-Tetrahydro-1-benzoxepin-5-amine

HRID 2271075

Reaction equation

HRID 2271075 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[N:12]O)[CH2:4][CH2:3][CH2:2]1.[BH4-].[Na+].O.N>COCCOC.[Ti](Cl)(Cl)(Cl)Cl>[NH2:12][CH:5]1[C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:1][CH2:2][CH2:3][CH2:4]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 4311764Sodium borohydrideHCID 732003533,4-dihydro-1-benzoxepin-5(2H)-one oxime

Product 1

HCID 156196982,3,4,5-Tetrahydro-1-benzoxepin-5-amineYield 113.9%

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 80711,2-DimethoxyethaneSolvent2×

Procedure

A solution of 2.0 g (11.3 mmol) of 3,4-dihydro-1-benzoxepin-5(2H)-one oxime in 15 ml of 1,2-dimethoxyethane (DME) was added dropwise at 0° C. under argon to a mixture of 4.5 g (23.7 mmol) of titanium tetrachloride and 1.79 g (47.4 mmol) of sodium borohydride in 50 ml of DME over the course of 20 min. After stirring at RT for 2 days, 100 ml of water were added dropwise and the mixture was rendered alkaline using conc. ammonia solution. After filtering off the precipitate with suction, the filtrate was extracted three times with EA. After washing with sodium chloride solution, drying over magnesium sulfate and concentrating, 2.1 g of 5-amino-2,3,4,5-tetrahydro-1-benzoxepine were obtained.

Workup

  1. filtrationAfter filtering off the precipitate with suction
  2. extractionthe filtrate was extracted three times with EA
  3. washAfter washing with sodium chloride solution
  4. dry with materialdrying over magnesium sulfate
  5. concentrationconcentrating

Sources & evidence

ORD record
ord-93b93d08e3624776bc1faf292198668e
Source dataset
uspto-grants-2001_12
Patent number
US06333349B1

Linked notes

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