Hydrochloric Acid → HCID 86749966, compound

HRID 1899374Notes

Reaction equation

HRID 1899374 reaction equation
[O:1]1[CH2:20][CH:2]1[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[C:14]3[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=3[O:12][N:11]=2)[CH2:6][CH2:5]1.FC1C=CC2C(C3CCNCC3)=NOC=2C=1.[ClH:37]>C(O)(C)C.C(O)C>[ClH:37].[ClH:37].[F:19][C:17]1[CH:16]=[CH:15][C:14]2[C:10]([CH:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH:2]([OH:1])[CH3:20])[CH2:5][CH2:6]3)=[N:11][O:12][C:13]=2[CH:18]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8494213-(4-Piperidyl)-6-fluoro-1,2-benzisoxazoleHCID 15285697N-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine

Product 1

HCID 86749966HCID 86749966, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
65 °C

Procedure

A stirred mixture of 1-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (1.19 g, 4.3 mmol) and 4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (0.95 g, 4.3 mmol) in isopropyl alcohol (50 ml) was heated at reflux for 1 hour, then stirred at 65° C. for 16 hours. The solvent was removed on a rotary evaporator. The solid residues were purified by flash chromatography over a silica gel column (SiO2, 35 g; eluted with methylene chloride, DCM, and CH3OH in DCM). The product thus obtained, weighted 2.55 g. This material was dissolved in ethanol and was treated with a solution of HCl (1M in ether). The salt collected weighed 2.35 g, m.p. >270° C. dec.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. customThe solvent was removed on a rotary evaporator
  4. customThe solid residues were purified by flash chromatography over a silica gel column (SiO2, 35 g; eluted with methylene chloride, DCM, and CH3OH in DCM)
  5. customThe product thus obtained
  6. customThe salt collected

Sources & evidence

ORD record
ord-93d2a62aef6c4553bfa874a6dd8cf511
Source dataset
uspto-grants-1996_11
Patent number
US05571803

Reaction notes

Loading…