Sodium Carbonate → HCID 13446113, compound

HRID 1277929Notes

Reaction equation

HRID 1277929 reaction equation
[BH4-].[Na+].[CH3:3][NH:4][C:5]1[CH2:6][O:7][C:8]2[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=2[C:10](=[O:12])[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C(O)(=O)C>[CH3:3][NH:4][CH:5]1[CH2:11][CH:10]([OH:12])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[O:7][CH2:6]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4311764Sodium borohydride2×HCID 134460473-(Methylamino)-1-benzoxepin-5(2H)-one

Product 1

HCID 13446113HCID 13446113, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

Sodium borohydride is added in small portions to a solution of 18.8 g (0.1 mole) 3-methylamino-1-benzoxepin-5-(2H)-one in a mixture of 125 ml dioxane and 125 ml acetic acid cooled in an ice bath. The reaction solution is maintained in a cooled state during the addition of the sodium borohydride (0.4 mole) up to the end of the reaction. The reaction solution is then poured into ice water, made alkaline with sodium carbonate and extracted with dichloromethane. The organic solution is washed with saturated salt solution and dried over sodium sulfate. After removal of the solvent, 16.4 g (85% of the theoretical yield) of racemic-2,3,4,5-tetrahydro-3-methylamino-1-benzoxepin-5-ol is recovered in the form of an oil.

Workup

  1. temperaturecooled in an ice bath
  2. extractionextracted with dichloromethane
  3. washThe organic solution is washed with saturated salt solution
  4. dry with materialdried over sodium sulfate
  5. customAfter removal of the solvent, 16.4 g (85% of the

Sources & evidence

ORD record
ord-31c7455639ee4d86a48beee68e931064
Source dataset
uspto-grants-1981_07
Patent number
US04279904

Reaction notes

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