Potassium Carbonate → 6,7-Dimethoxy-2-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-hydroxy-1-propyl]1,2,3,4-tetrahydroisoquinoline

HRID 1449989Notes

Reaction equation

HRID 1449989 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.C([O-])([O-])=O.[K+].[K+].Cl.[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[CH2:36][NH:35][CH2:34][CH2:33]2>C(O)(C)C>[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[CH2:36][N:35]([CH2:20][CH:2]([OH:1])[CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([C:10]3[C:14]4[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:13]=4[O:12][N:11]=3)[CH2:6][CH2:5]1)[CH2:34][CH2:33]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 64560356,7-Dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 15285697N-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine

Product 1

HCID 152856806,7-Dimethoxy-2-[3-[4-(6-fluoro-1,2-benzisoxazol-3-yl)-1-piperidinyl]-2-hydroxy-1-propyl]1,2,3,4-tetrahydroisoquinolineYield 11%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A stirred mixture of 1-(2,3-epoxypropyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (3.2 g, 11.6 mmol), K2CO3 (2 gm, 1.25 eq) and 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (3.3 g, 1.25 eq) in isopropyl alcohol (200 ml) was heated at reflux for 6 hours. The mixture was cooled and filtered. The solvent was removed to about 50 ml and the solution was allowed to stand overnight. Crystals (0.6 g) formed and were collected. The mother liquor was concentrated to a white solid. Recrystallization twice from ethanol yielded the product (1.95 g, m.p. 153°-154° C. ANALYSIS: Calculated for C26H32FN3O4 : 66.51%C 6.87%H 8.95%N Found: 66.51%C 7.05%H 8.83%N

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. customThe solvent was removed to about 50 ml

Sources & evidence

ORD record
ord-5aacab8a45044a62ba4781bda9f9004a
Source dataset
uspto-grants-1997_02
Patent number
US05599821

Reaction notes

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