Hydrochloric Acid → HCID 21959992, compound

HRID 1872975Notes

Reaction equation

HRID 1872975 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=3[O:14][N:13]=2)[CH2:8][CH2:7]1.[C@@H:22]12[C:31](=O)[O:30][C:28](=[O:29])[C@@H:23]1[CH2:24][CH2:25][CH2:26][CH2:27]2.[ClH:33]>N1C=CC=CC=1.C(O)C>[ClH:33].[F:21][C:19]1[CH:18]=[CH:17][C:16]2[C:12]([CH:9]3[CH2:10][CH2:11][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:1]4[C:28](=[O:29])[CH:23]5[CH:22]([CH2:27][CH2:26][CH2:25][CH2:24]5)[C:31]4=[O:30])[CH2:7][CH2:8]3)=[N:13][O:14][C:15]=2[CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 641660Hexahydrophthalic anhydride, cis-HCID 219600491-(4-Aminobutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine

Product 1

HCID 21959992HCID 21959992, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1049PyridineSolvent2×

Procedure

A mixture of 1-(4-aminobutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (4.7 g, 16.1 mmol) and cis-1,2-cyclohexanedicarboxylic anhydride (3.23 g, 21 mmol) in pyridine (45 ml) was heated at reflux for 8 hours. At the end of the reaction, pyridine was removed to dryness. The crude product was purified on a silica gel column. The material thus obtained weighed 3.18 g (45%) as a clear oil. This oil was dissolved in ethanol (15 ml), then was treated with HCl in ethanol (45 ml). Crystallization took place upon cooling. The crystals were collected, 3.2 g, m.p.=229-231° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. customwas removed to dryness
  4. customThe crude product was purified on a silica gel column
  5. customThe material thus obtained
  6. customCrystallization
  7. temperatureupon cooling
  8. customThe crystals were collected

Sources & evidence

ORD record
ord-17220d9b11f44d388225e53192d7c8f0
Source dataset
uspto-grants-2000_08
Patent number
US06110938

Reaction notes

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