Dichloromethane → 4-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butyl decanoate fumarate

HRID 55641Notes

Reaction equation

HRID 55641 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH2:11][CH2:10]3)=[N:7][O:8][C:4]=2[CH:3]=1.C(N([CH2:27][CH3:28])CC)C.C(Cl)Cl.[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36]>C(O)C>[C:32]([OH:39])(=[O:38])/[CH:33]=[CH:34]/[C:35]([OH:37])=[O:36].[C:32]([O:19][CH2:18][CH2:17][CH2:16][CH2:15][N:12]1[CH2:13][CH2:14][CH:9]([C:6]2[C:5]3[CH:20]=[CH:21][C:2]([F:1])=[CH:3][C:4]=3[O:8][N:7]=2)[CH2:10][CH2:11]1)(=[O:39])[CH2:33][CH2:34][CH2:35][CH2:21][CH2:2][CH2:3][CH2:4][CH2:27][CH3:28]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 444972Fumaric AcidHCID 219600384-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butanol

Product 1

HCID 219600094-[4-(6-Fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butyl decanoate fumarate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]butanol (2.0 g, 6.84 mmol), triethylamine (1,0 g, 10 mmol) in DCM (70 ml) decanoyl chloride (1.7 g, 8.9 mmol) was added dropwise at room temperature. The mixture was stirred for 1 hour., then was concentrated to a crude solid. The solid was extracted into ethyl acetate, and the insoluble salts were filtered. The solvents were removed. The crude product was purified by flash chromatography (Sorbsil C-30, 30 g, eluted with a mixture of MeOH in DCM). The oil thus obtained (2.5 g, 81%) was converted to a fumarate salt with fumaric acid (650 mg, 1.0 eq) in ethanol. Crystals were collected: 1.48 g, m.p.=109°-110° C.

Workup

  1. concentration, then was concentrated to a crude solid
  2. extractionThe solid was extracted into ethyl acetate
  3. filtrationthe insoluble salts were filtered
  4. customThe solvents were removed
  5. customThe crude product was purified by flash chromatography (Sorbsil C-30, 30 g
  6. washeluted with a mixture of MeOH in DCM)
  7. customThe oil thus obtained (2.5 g, 81%)
  8. customCrystals were collected

Sources & evidence

ORD record
ord-acea169575f84529b1cdb1665c3bad54
Source dataset
uspto-grants-1997_04
Patent number
US05624927

Reaction notes

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