HCID 18620894, compound → HCID 18620610, compound

HRID 1861700Notes

Reaction equation

HRID 1861700 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:23][CH2:22][CH2:21][N:20](C=O)[CH2:19][C:18]=3[CH:26]=2)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>CO.Cl>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:15]=[CH:16][C:17]3[O:23][CH2:22][CH2:21][NH:20][CH2:19][C:18]=3[CH:26]=2)=[O:13])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 18620894HCID 18620894, compound

Product 1

HCID 18620610HCID 18620610, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of the 3-(1-acetyl-4-piperidinyl)-1-(4-formyl 2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1-propanone (6.77 g) in methanol (100 ml) and concentrated hydrochloric acid (100 ml) were heated together at 80-85° C. for 2 hours. The methanol was then distilled off and the residual aqueous solution was made basic with saturated aqueous solution of potassium carbonate and extracted with ethyl acetate-tetrahydrofuran (2:1). The extract was washed with saturated NaCl/H2O and dried over MgSO4, and the solvent was distilled off under reduced pressure to provide 3-(1-acetyl-4-piperidinyl)-1-(2,3,4,5-tetrahydro-1,4-benzoxazepin-7-yl)-1-propanone (6.04 g) as light-yellow oil.

Workup

  1. distillationThe methanol was then distilled off
  2. extractionextracted with ethyl acetate-tetrahydrofuran (2:1)
  3. washThe extract was washed with saturated NaCl/H2O
  4. dry with materialdried over MgSO4
  5. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-77dee05df1d5494092ea0f901055e6eb
Source dataset
uspto-grants-2003_03
Patent number
US06534496B1

Reaction notes

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