Methanol → HCID 131720728, compound

HRID 964936Notes

Reaction equation

HRID 964936 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[O:6][C:7]3[CH:30]=[CH:29][CH:28]=[CH:27][C:8]=3[C@@H:9]3[CH2:13][C@@H:12]([CH2:14][N:15]4[CH2:20][CH2:19][N:18]([C:21](=[O:26])C(F)(F)F)[CH2:17][CH2:16]4)[O:11][N:10]3[C:4]=2[CH:3]=1.[C:33](=[O:36])([O-:35])[O-].[K+].[K+].C[OH:40]>O>[C:21]([OH:26])(=[O:40])[C:33]([OH:35])=[O:36].[Cl:1][C:2]1[CH:32]=[CH:31][C:5]2[O:6][C:7]3[CH:30]=[CH:29][CH:28]=[CH:27][C:8]=3[C@@H:9]3[CH2:13][C@@H:12]([CH2:14][N:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[O:11][N:10]3[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 86752845HCID 86752845, compound

Product 1

HCID 131720728HCID 131720728, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (±)-cis-1-[(11-chloro-3,3a-dihydro-2H-dibenz[b,f]isoxazolo[2,3-d][1,4]-oxazepin-2-yl)methyl]-4-(trifluoroacetyl)piperazine (7.1 g), prepared following the procedure of example 7, and potassium carbonate (4.2 g) in methanol (300 ml) and water (43 ml) was stirred at RT for 2 hours. The solvent was evaporated. The residue was treated with water, extracted with CH2Cl2 and the separated organic layer was evaporated. The residue (5.1 g) was purified by flash chromatography over silica gel (eluent: CH2Cl2 /CH3OH 9/1, 8/2 to 7/3) and the pure fractions were collected and evaporated. The residue (4.2g) was converted into the oxalic acid salt (2:3) in C2H5OH at room temperature, yielding 3.9 g (47%) of (±)-cis- 11-chloro-3,3a-dihydro-2-(1-piperazinylmethyl)-2H-dibenz[b,f]isoxazolo[2,3-d][1,4]oxazepine ethanedioate(2:3); mp. >250.0° C. (comp. 3).

Workup

  1. customprepared
  2. customThe solvent was evaporated
  3. additionThe residue was treated with water
  4. extractionextracted with CH2Cl2
  5. customthe separated organic layer was evaporated
  6. customThe residue (5.1 g) was purified by flash chromatography over silica gel (eluent: CH2Cl2 /CH3OH 9/1, 8/2 to 7/3)
  7. customthe pure fractions were collected
  8. customevaporated
  9. customwas converted into the oxalic acid salt (2:3) in C2H5OH at room temperature

Sources & evidence

ORD record
ord-e21271a06f0e4b7482a49797d04fab4b
Source dataset
uspto-grants-1998_06
Patent number
US05773433

Reaction notes

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