Sodium Hydroxide → 3-(2-piperidinopropyl)-4-(3-hydroxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

HRID 26432Notes

Reaction equation

HRID 26432 reaction equation
[N:1]1([CH:7]([CH3:25])[CH2:8][C:9]2[C:10](=[O:24])[NH:11][CH2:12][CH2:13][CH2:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([O:22]C)[CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)Cl>[N:1]1([CH:7]([CH3:25])[CH2:8][C:9]2[C:10](=[O:24])[NH:11][CH2:12][CH2:13][CH2:14][C:15]=2[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[CH:17]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 203329443-(2-piperidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Product 1

HCID 203329453-(2-piperidinopropyl)-4-(3-hydroxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of 6.15 g of 3-(2-piperidinopropyl)-4-(3-methoxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone in 60 ml of methylene chloride, cooled in a dry ice-acetone bath, is added slowly to 120 ml of a similarly precooled 10% solution of boron tribromide in methylene chloride. The mixture is allowed to warm to room temperature and stirred for four hours. It is again cooled in an ice bath, 120 ml of 3 N aqueous sodium hydroxide are added and stirring at room temperature is continued for 30 minutes. The aqueous layer is separated and the methylene chloride solution is washed with 60 ml of water. The combined aqueous solution is neutralized to pH=9-10 with 6 N hydrochloric acid and the precipitate collected, to yield the 3-(2-piperidinopropyl)-4-(3-hydroxyphenyl)-1,5,6,7-tetrahydro-2H-azepinone melting at 218°-220°.

Workup

  1. temperatureIt is again cooled in an ice bath
  2. stirringstirring at room temperature
  3. waitis continued for 30 minutes
  4. customThe aqueous layer is separated
  5. washthe methylene chloride solution is washed with 60 ml of water
  6. customthe precipitate collected

Sources & evidence

ORD record
ord-bffedf3fb2ab4d5d9d4add8f5bbaf057
Source dataset
uspto-grants-1979_04
Patent number
US04150129

Reaction notes

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