1-Propanol → Mono-2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl)piperazinium-1-yl]ethoxy)ethanol trans-butenedioate

HRID 2244554Notes

Reaction equation

HRID 2244554 reaction equation
Cl.[N:2]1([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:23](=[O:26])([O-:25])[O-:24].[Na+].[Na+].Cl[CH2:30][CH2:31][O:32][CH:33]([OH:35])[CH3:34].C(O)CC>[I-].[Na+].C(OCC)(=O)C.CN1CCCC1=O>[C:33]([OH:35])(=[O:32])/[CH:34]=[CH:3]/[C:23]([OH:25])=[O:26].[OH:24][CH2:30][CH2:31][O:32][CH2:33][CH2:34][N:5]1[CH2:4][CH2:3][N:2]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[S:12][C:11]3[CH:19]=[CH:20][CH:21]=[CH:22][C:10]=3[N:9]=2)[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 10311-PropanolHCID 10340Sodium CarbonateHCID 162023916-Piperazin-1-ylbenzo[b][1,4]benzothiazepine;hydrochlorideHCID 221454452-Chloroethoxyethanol

Product 1

HCID 6918224Mono-2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl)piperazinium-1-yl]ethoxy)ethanol trans-butenedioateYield 115.3%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

11-piperazinyl-dibenzo[b,f][1,4]thiazepine hydrochloride (40 g) obtained in step c), sodium carbonate (69.3 g), sodium iodide (0.65 g), and 2-chloroethoxyethanol (14.7 g) were added to a solution of n-propyl alcohol (260 ml) and N-methylpyrrolidone (65 ml), and reflux was conducted for 24 hours. Ethyl acetate (327 ml) was added thereto, washing was conducted using water (2×1000 ml), an organic layer was separated to be dried with magnesium sulfate, and a solvent was removed at reduced pressure, thereby oil was created. The resulting oil was completely dissolved in ethanol, and fumaric acid (7.1 g) was added thereto, to produce 11-[4-[2-(hydroxyethoxy)ethyl]-1-piperazinyl]-dibenzo[b,f][1,4]thiazepine fumarate (34 g).

Workup

  1. temperaturereflux
  2. washwashing
  3. customan organic layer was separated
  4. dry with materialto be dried with magnesium sulfate
  5. customa solvent was removed at reduced pressure
  6. dissolutionThe resulting oil was completely dissolved in ethanol
  7. additionfumaric acid (7.1 g) was added

Sources & evidence

ORD record
ord-304e9613a1bb457c9046b0214da8909f
Source dataset
uspto-grants-2010_03
Patent number
US07678902B2

Reaction notes

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